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58-14-0

Basic Information
CAS No.: 58-14-0
Name: Pyrimethamine
Article Data: 18
Molecular Structure:
Molecular Structure of 58-14-0 (Pyrimethamine)
Formula: C12H13ClN4
Molecular Weight: 248.715
Synonyms: 2,4-Diamino-5-(p-chlorophenyl)-6-ethylpyrimidine;5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidinediamine;
EINECS: 200-364-2
Density: 1.305 g/cm3
Melting Point: 233-234°C
Boiling Point: 491.5 °C at 760 mmHg
Flash Point: 251 °C
Solubility: Insoluble in water
Appearance: white solid
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 26
Transport Information: UN 3249
PSA: 77.82000
LogP: 3.68620
Synthetic route
95458-40-5

2,4-diamino-5-(3-azido-4-chlorophenyl)-6-ethylpyrimidine

58-14-0

2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine

Conditions
ConditionsYield
With hydrazine hydrate for 0.25h; Heating;85%
1679-18-1

4-Chlorophenylboronic acid

514854-13-8

2,4-diamino-6-ethyl-5-iodopyrimidine

58-14-0

2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; Pd(OAc)2(dppf)2 In 1,2-dimethoxyethane for 24h; Suzuki cross-coupling; Heating;76%
17039-14-4

5-(4-chlorophenyl)pyrimidine-2,4-diamine

4433-63-0

Ethyl boronic acid

58-14-0

2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine

Conditions
ConditionsYield
Stage #1: 5-(4-chlorophenyl)pyrimidine-2,4-diamine With acetic acid; trifluoroacetic acid In acetonitrile at 20℃; for 0.166667h; Minisci Aromatic Substitution; Green chemistry;
Stage #2: Ethyl boronic acid With oxygen In acetonitrile at 110℃; under 760.051 Torr; for 10h; Minisci Aromatic Substitution; Green chemistry;
74%

C12H12ClN6(1+)*BF4(1-)

58-14-0

2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine

Conditions
ConditionsYield
With formamide; triethylamine Ambient temperature;64%

1-(4-chlorophenyl)-1-cyano-2-methoxybut-1-ene

50-01-1

guanidine hydrochloride

58-14-0

2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine

Conditions
ConditionsYield
With sodium methylate In various solvent(s) for 16h; Heating;50%
55474-40-3

α-(4-chlorophenyl)-α-propionylacetonitrile

58-14-0

2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine

Conditions
ConditionsYield
With diethyl ether anschliessenden Erwaermen mit Guanidin in Aethanol;
105640-59-3

6-ethyl-2-amino-5-(4-chloro-phenyl)-3H-pyrimidine-4-thione

58-14-0

2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine

Conditions
ConditionsYield
With ethanol; ammonia at 180℃;
100716-90-3

N-[4-ethyl-6-chloro-5-(4-chloro-phenyl)-pyrimidin-2-yl]-acetamide

58-14-0

2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine

Conditions
ConditionsYield
With ethanol; ammonia at 155℃;
With ammonia; phenol at 110℃;
67466-67-5

2-(4-chloro-phenyl)-3-isobutoxy-pent-2-enenitrile

141-52-6

sodium ethanolate

506-93-4

guanidine nitrate

58-14-0

2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine

Conditions
ConditionsYield
With ethanol

3-anilino-2-(4-chloro-phenyl)-pent-2-enenitrile

78-39-7

Triethyl orthoacetate

58-14-0

2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine

Conditions
ConditionsYield
anschliessenden Erhitzen mit Guanidin in Aethanol auf 130grad/2 Torr;
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Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 13 ,1977,p. 233.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (feed); Inadequate Studies: mouse NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-77 ,1978. ; (feed); No Evidence: rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-77 ,1978. . EPA Genetic Toxicology Program.

Specification

The Pyrimethamine, with the CAS registry number 58-14-0 and EINECS registry number 200-364-2, has the systematic name of 5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine. It is also called Daraprim, and the molecular formula of this chemical is C12H13ClN4. It is a kind of white solid, and harmful if swallowed, so you had better be careful. It is sensitive to exposure to light, and insoluble in water. What's more, it should be stored at 0-6°C.

The physical properties of Pyrimethamine are as following: (1)ACD/LogP: 2.75; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.49; (4)ACD/LogD (pH 7.4): 2.66; (5)ACD/BCF (pH 5.5): 3.95; (6)ACD/BCF (pH 7.4): 58.84; (7)ACD/KOC (pH 5.5): 40.66; (8)ACD/KOC (pH 7.4): 606.32; (9)#H bond acceptors: 4; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 32.26 Å2; (13)Index of Refraction: 1.655; (14)Molar Refractivity: 69.94 cm3; (15)Molar Volume: 190.4 cm3; (16)Polarizability: 27.72×10-24cm3; (17)Surface Tension: 61.3 dyne/cm; (18)Density: 1.305 g/cm3; (19)Flash Point: 251 °C; (20)Enthalpy of Vaporization: 75.82 kJ/mol; (21)Boiling Point: 491.5 °C at 760 mmHg; (22)Vapour Pressure: 8.34E-10 mmHg at 25°C.

Applications of Pyrimethamine: It is a medication used for protozoal infections,. It is commonly used as an antimalarial drug (for both treatment and prevention of malaria). and combined with sulfadiazine, it can be used in the treatment of Toxoplasma gondii infections in immunocompromised patients, such as HIV-positive individuals. What's more, it is one of the folic acid antagonists that is used as an antimalarial or with a sulfonamide to treat toxoplasmosis.

Uses of Pyrimethamine: It can react with butyric acid anhydride to produce N-[2-butyrylamino-5-(4-chloro-phenyl)-6-ethyl-pyrimidin-4-yl]-butyramide. This reaction will need heating, and the yield is about 77%.

Pyrimethamine can react with butyric acid anhydride to produce N-[2-butyrylamino-5-(4-chloro-phenyl)-6-ethyl-pyrimidin-4-yl]-butyramide

You can still convert the following datas into molecular structure:
(1)SMILES: Clc2ccc(c1c(nc(nc1CC)N)N)cc2
(2)InChI: InChI=1/C12H13ClN4/c1-2-9-10(11(14)17-12(15)16-9)7-3-5-8(13)6-4-7/h3-6H,2H2,1H3,(H4,14,15,16,17)
(3)InChIKey: WKSAUQYGYAYLPV-UHFFFAOYAW

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LDLo intraperitoneal 75mg/kg (75mg/kg)   United States Patent Document. Vol. #3919229,
hamster LDLo oral 250mg/kg (250mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Teratology, The International Journal of Abnormal Development. Vol. 4, Pg. 205, 1971.
infant TDLo unreported 19mg/kg/31D-I (19mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA

BLOOD: NORMOCYTIC ANEMIA
Journal of Analytical Toxicology. Vol. 17, Pg. 248, 1993.
mouse LD50 intraperitoneal 74mg/kg (74mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 9, Pg. 658, 1974.
mouse LD50 oral 92mg/kg (92mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 6, Pg. 185, 1951.
mouse LDLo subcutaneous 160mg/kg (160mg/kg)   Journal of Medicinal Chemistry. Vol. 16, Pg. 1399, 1973.
rat LD50 intraperitoneal 70mg/kg (70mg/kg)   "International Congress of Chemotherapy, Proceedings of the 3rd Congress, 1963," Kuemmerle, H.P., and Prezios, P., Stuttgart, Fed. Rep. Ger., Georg Thieme Verlag, 1964Vol. -, Pg. 367, 1964.
rat LD50 oral 440mg/kg (440mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Journal of Chemotherapy. Vol. 5, Pg. 400, 1993.