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Pyrimethamine

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Identification
Molecular formula
C12H13ClN4
CAS number
58-14-0
IUPAC name
5-(4-chlorophenyl)-6-ethyl-pyrimidine-2,4-diamine
State
State

Pyrimethamine is a solid at room temperature.

Melting point (Celsius)
233.00
Melting point (Kelvin)
506.15
Boiling point (Celsius)
337.00
Boiling point (Kelvin)
610.15
General information
Molecular weight
248.72g/mol
Molar mass
248.6950g/mol
Density
1.3100g/cm3
Appearence

Pyrimethamine is typically a white crystalline powder. It is slightly soluble in water, but more soluble in organic solvents.

Comment on solubility

Solubility of 5-(4-chlorophenyl)-6-ethyl-pyrimidine-2,4-diamine

The solubility of 5-(4-chlorophenyl)-6-ethyl-pyrimidine-2,4-diamine (C12H13ClN4) is influenced by several factors related to its chemical structure. This compound, containing a pyrimidine ring and a chlorophenyl group, presents characteristics typical of organic compounds with limited solubility in water.

Factors affecting solubility:

  • Polarity: The presence of polar functional groups can enhance solubility. However, in this compound, the chlorine atom and the ethyl group can reduce overall polarity.
  • Hydrogen bonding: The amine groups may provide some capacity for hydrogen bonding, which can slightly increase solubility in polar solvents.
  • Molecular size: The relatively large size of the molecule can contribute to solubility challenges, especially in aqueous environments.

Generally, it is observed that this compound is sparingly soluble in water, while it may exhibit better solubility in organic solvents such as dimethyl sulfoxide (DMSO) or ethanol. This behavior is typical for many compounds that contain extensive aromatic systems, which tend to be more soluble in non-polar solvents.

In summary, the solubility of 5-(4-chlorophenyl)-6-ethyl-pyrimidine-2,4-diamine is limited in water but may be more favorable in organic solvents, demonstrating a classic example of how chemical structure dictates solubility characteristics.

Interesting facts

Interesting Facts About 5-(4-Chlorophenyl)-6-ethyl-pyrimidine-2,4-diamine

5-(4-Chlorophenyl)-6-ethyl-pyrimidine-2,4-diamine is a fascinating compound that captures the attention of both chemists and pharmacologists due to its structure and potential applications. Here are some insightful details:

  • Pyrimidine Framework: The compound contains a pyrimidine ring, which is a key feature in many biological molecules, including nucleic acids. This structure contributes to its biological activity.
  • Chlorophenyl Substituent: The presence of a 4-chlorophenyl group can significantly influence the compound's properties, including its lipophilicity and binding affinities to various biological targets.
  • Pharmacological Potential: Compounds like this one are often investigated for their role as potential therapeutic agents. They could serve as inhibitors in various pathways, making them interesting candidates for drug development.
  • Structure-Activity Relationship (SAR): Researchers focus on this aspect to understand how modifications to the compound's structure can enhance its efficacy or reduce side effects, revealing the compound's versatility.
  • Synthetic Challenges: The synthesis of such complex structures often involves multiple steps which can pose challenges in terms of yield and purity, making them a topic of research in synthetic organic chemistry.

Overall, 5-(4-chlorophenyl)-6-ethyl-pyrimidine-2,4-diamine stands as an intriguing member of the pyrimidine family, bridging the gap between structure and function in medicinal chemistry. Its unique features continue to fuel research into its potential applications in health sciences.

Synonyms
pyrimethamine
58-14-0
Daraprim
Chloridine
5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
Diaminopyritamin
Ethylpyrimidine
Pirimecidan
Pirimetamin
Pirimetamina
Chloridin
Chloridyn
Darachlor
Erbaprelina
Khloridin
Primethamine
Pyrimethamin
Malocid
Malocide
Tindurin
Pyrimethaminum
Darapram
Daraprime
Malacid
5-(4-CHLOROPHENYL)-6-ETHYL-2,4-PYRIMIDINEDIAMINE
Pyremethamine
2,4-Pyrimidinediamine, 5-(4-chlorophenyl)-6-ethyl-
Daraclor
Maloprim
2,4-Diamino-5-(p-chlorophenyl)-6-ethylpyrimidine
TCMDC-125860
2,4-Diamino-5-chlorophenyl-6-ethylpyrimidine
BW 50-63
2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
RP 4753
NCI-C01683
5-(4'-Chlorophenyl)-2,4-diamino-6-ethylpyrimidine
GNF-Pf-5586
WR 2978
Pirimetamina [INN-Spanish]
Pyrimethaminum [INN-Latin]
NSC-3061
5-(4-Chlorophenyl)-6-ethyl-2,4-diaminopyrimidine
CCRIS 546
4753 R.P.
NSC 3061
EINECS 200-364-2
UNII-Z3614QOX8W
BRN 0219864
CHEBI:8673
Z3614QOX8W
DTXSID9021217
2,4-Pyrimidinediamine, 5-(p-chlorophenyl)-6-ethyl-
AI3-25005
HSDB 8042
NSC3061
Pyrimidine, 2,4-diamino-5-(p-chlorophenyl)-6-ethyl-
TCMDC-123831
CHEMBL36
5-(4-CHLORO-PHENYL)-6-ETHYL-PYRIMIDINE-2,4-DIAMINE
RP-4753
WR-2978
MLS000028606
MLS002701881
DTXCID601217
Pyrimethamine [USP:INN:BAN:JAN]
FANSIDAR COMPONENT PYRIMETHAMINE
CAS-58-14-0
NCGC00016256-08
SMR000058714
Tinduring
Pirimetamina [Spanish]
Pirimetamina (INN-Spanish)
Pyrimethaminum (INN-Latin)
PYRIMETHAMINE (IARC)
PYRIMETHAMINE [IARC]
CP6
PYRIMETHAMINE (MART.)
PYRIMETHAMINE [MART.]
5-(4-chlorophenyl)-6-ethyl-pyrimidine-2,4-diamine
PYRIMETHAMINE (USP-RS)
PYRIMETHAMINE [USP-RS]
BRD9204
BRD-9204
Pyrimethamine (USP:INN:BAN:JAN)
PYRIMETHAMINE (EP MONOGRAPH)
PYRIMETHAMINE [EP MONOGRAPH]
PYRIMETHAMINE (USP MONOGRAPH)
PYRIMETHAMINE [USP MONOGRAPH]
Daraprim (TN)
Pyrimethamine (Pyr)
SR-01000003150
MFCD00057350
CRL-8131 & Pyrimethamine
CRL-8142 & Pyrimethamine
Lactoferrin B & Pyrimethamine
Lactoferrin H & Pyrimethamine
Pyrimethamine (JAN/USP/INN)
AZT + Pyrimethamine combination
EXR-101
5-(p-chlorophenyl)-6-ethyl-2,4-diaminopyrimidine
Prestwick_504
5-(4-chlorophenyl)-2,4-diamino-6-ethylpyrimidine
BW 5063
Daraclor (Salt/Mix)
Spectrum_000906
4km0
CPD000058714
Pyrimethamine (Standard)
Opera_ID_1437
Prestwick0_000037
Prestwick1_000037
Prestwick2_000037
Prestwick3_000037
Spectrum2_000886
Spectrum3_001701
Spectrum4_000494
Spectrum5_001447
PYRIMETHAMINE [MI]
PYRIMETHAMINE [INN]
PYRIMETHAMINE [JAN]
cid_4993
NCIOpen2_008313
BIDD:PXR0173
SCHEMBL25129
BSPBio_000133
BSPBio_003282
KBioGR_001007
KBioSS_001386
PYRIMETHAMINE [VANDF]
MLS001148621
MLS002454446
BIDD:GT0149
DivK1c_000652
SPECTRUM1500520
SPBio_000672
SPBio_002054
PYRIMETHAMINE [WHO-DD]
PYRIMETHAMINE [WHO-IP]
BPBio1_000147
GTPL4800
BDBM18512
HMS502A14
KBio1_000652
KBio2_001386
KBio2_003954
KBio2_006522
KBio3_002502
P01BD01
NINDS_000652
Pirimecidan;Pirimetamin;RP 4753
HMS1568G15
HMS1920N12
HMS2092E13
HMS2095G15
HMS2235A17
HMS3259C04
HMS3371L07
HMS3655D09
HMS3675P11
HMS3712G15
HMS3743O05
HMS3871I03
Pharmakon1600-01500520
PYRIMETHAMINE [GREEN BOOK]
PYRIMETHAMINE [ORANGE BOOK]
2, 5-(p-chlorophenyl)-6-ethyl-
PXB93699
2, 5-(4-chlorophenyl)-6-ethyl-
Tox21_110332
Tox21_201834
Tox21_300129
CCG-39626
HY-18062R
NSC757306
PYRIMETHAMINUM [WHO-IP LATIN]
AKOS015892534
Tox21_110332_1
AB02313
AC-7879
CS-1717
DB00205
FP27346
KS-5223
NC00528
NSC-757306
IDI1_000652
NCGC00016256-01
NCGC00016256-02
NCGC00016256-03
NCGC00016256-04
NCGC00016256-05
NCGC00016256-06
NCGC00016256-07
NCGC00016256-09
NCGC00016256-10
NCGC00016256-11
NCGC00016256-12
NCGC00016256-13
NCGC00016256-14
NCGC00016256-16
NCGC00016256-17
NCGC00023188-03
NCGC00023188-04
NCGC00023188-05
NCGC00023188-06
NCGC00023188-07
NCGC00254199-01
NCGC00259383-01
WLN: T6N CNJ BZ DZ ER DG& F2
HY-18062
NCI60_002604
PYRIMETHAMINE COMPONENT OF FANSIDAR
SBI-0051500.P003
DB-053158
AB00052084
NS00001824
P2037
S2006
SW196698-3
5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidine
C07391
D00488
EN300-118717
MLS-0002822.0001
2,4-diamino-5-p-chlorophenyl-6-ethylpyrimidine
AB00052084-21
AB00052084_22
AB00052084_25
2,4-diamino-5(4-chlorophenyl)-6-ethylpyrimidine
2,4-Diamono-5-(p-chlorophenyl)-6-ethylpyrimidine
L000713
Pyrimethamine, VETRANAL(TM), analytical standard
Pyrimidine,4-diamino-5-(p-chlorophenyl)-6-ethyl-
Q421072
2,4,-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
2,4-diamino-5-(4-chloro-phenyl)-6-ethylpyrimidine
2,4-diamino-6-ethyl-5-(4-chlorophenyl)pyrimidine
SR-01000003150-2
SR-01000003150-4
BRD-K88429204-001-05-4
BRD-K88429204-001-18-7
BRD-K88429204-001-21-1
BRD-K88429204-001-33-6
BRD-K88429204-001-34-4
BRD-K88429204-001-35-1
BRD-K88429204-001-36-9
Z1515385085
5-(P-CHLOROPHENYL)-6-ETHYL-2,4-PYRIMIDINEDIAMINE
Pyrimethamine, European Pharmacopoeia (EP) Reference Standard
Pyrimethamine, United States Pharmacopeia (USP) Reference Standard
200-364-2
5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidinediamine;2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidine;Chloridin