2,4-diamino-5-(3-azido-4-chlorophenyl)-6-ethylpyrimidine
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
With hydrazine hydrate for 0.25h; Heating; | 85% |
4-Chlorophenylboronic acid
2,4-diamino-6-ethyl-5-iodopyrimidine
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; Pd(OAc)2(dppf)2 In 1,2-dimethoxyethane for 24h; Suzuki cross-coupling; Heating; | 76% |
5-(4-chlorophenyl)pyrimidine-2,4-diamine
Ethyl boronic acid
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
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% |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
With formamide; triethylamine Ambient temperature; | 64% |
Conditions | Yield |
---|---|
With sodium methylate In various solvent(s) for 16h; Heating; | 50% |
diazomethane
α-(4-chlorophenyl)-α-propionylacetonitrile
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
With diethyl ether anschliessenden Erwaermen mit Guanidin in Aethanol; |
6-ethyl-2-amino-5-(4-chloro-phenyl)-3H-pyrimidine-4-thione
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
With ethanol; ammonia at 180℃; |
N-[4-ethyl-6-chloro-5-(4-chloro-phenyl)-pyrimidin-2-yl]-acetamide
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
With ethanol; ammonia at 155℃; | |
With ammonia; phenol at 110℃; |
2-(4-chloro-phenyl)-3-isobutoxy-pent-2-enenitrile
sodium ethanolate
guanidine nitrate
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
With ethanol |
Conditions | Yield |
---|---|
anschliessenden Erhitzen mit Guanidin in Aethanol auf 130grad/2 Torr; |
Diacetamidopyrimethamine
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
With zinc(II) chloride In ethanol for 2h; Ambient temperature; |
N-[5-(4-Chloro-phenyl)-2-(2,2-dimethyl-propionylamino)-6-ethyl-pyrimidin-4-yl]-2,2-dimethyl-propionamide
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
With zinc(II) chloride In ethanol for 2h; Heating; | |
Multi-step reaction with 3 steps 1: ZnCl2 / ethanol / 2 h / Heating 2: 76 percent / Heating 3: ZnCl2 / ethanol / 6 h / Heating View Scheme |
C26H21ClN4O2
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
With zinc(II) chloride In ethanol for 6h; Heating; | |
Multi-step reaction with 3 steps 1: ZnCl2 / ethanol / 6 h / Heating 2: 62 percent / Heating 3: ZnCl2 / ethanol / 2 h / Heating View Scheme |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
With ethanol; ammonia at 130℃; |
Conditions | Yield |
---|---|
With ethanol anschliessenden Erhitzen mit Guanidin in Aethanol auf 130grad/2 Torr; |
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 80℃; for 0.0833333h; | 0.70 g |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 90 percent / POCl3 / Heating 2: 35 percent aq. NH3 3: 56 percent / I2; aq. NaOH / CHCl3 / 5 h 4: 76 percent / Pd(OAc)2(dppf)2; aq. K2HPO4 / 1,2-dimethoxy-ethane / 24 h / Heating View Scheme |
2,4-diamino-6-ethylpyrimidine
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 56 percent / I2; aq. NaOH / CHCl3 / 5 h 2: 76 percent / Pd(OAc)2(dppf)2; aq. K2HPO4 / 1,2-dimethoxy-ethane / 24 h / Heating View Scheme |
2-amino-4-chloro-6-ethylpyrimidine
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 35 percent aq. NH3 2: 56 percent / I2; aq. NaOH / CHCl3 / 5 h 3: 76 percent / Pd(OAc)2(dppf)2; aq. K2HPO4 / 1,2-dimethoxy-ethane / 24 h / Heating View Scheme |
α-(4-chlorophenyl)-α-propionylacetonitrile
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dioxane / 20 °C 2: 0.70 g / dimethylsulfoxide / 0.08 h / 80 °C View Scheme | |
Multi-step reaction with 2 steps 1: 100 °C 2: anschliessenden Erhitzen mit Guanidin in Aethanol auf 130grad/2 Torr View Scheme | |
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid; toluene 2: ethanol View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: LDA / tetrahydrofuran / 0.17 h / -78 °C 1.2: 62 percent / tetrahydrofuran / -78 °C 2.1: dioxane / 20 °C 3.1: 0.70 g / dimethylsulfoxide / 0.08 h / 80 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium ethylate 2: 100 °C 3: anschliessenden Erhitzen mit Guanidin in Aethanol auf 130grad/2 Torr View Scheme | |
Multi-step reaction with 2 steps 1: sodium ethylate 2: diethyl ether / anschliessenden Erwaermen mit Guanidin in Aethanol View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium ethanolate / ethanol / 4 h / 80 °C 2.1: sodium hydride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere 2.2: 5 h / 0 - 20 °C / Inert atmosphere 3.1: sodium ethanolate / ethanol / 10 h / 80 °C 4.1: trifluoroacetic acid; acetic acid / acetonitrile / 0.17 h / 20 °C / Green chemistry 4.2: 10 h / 110 °C / 760.05 Torr / Green chemistry View Scheme |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 95 percent / 0.5M aq. HCl / 0.08 h / Heating 2: 1.) NaNO2, 5M aq. HCl; 2.) NaN3 / 1.) 0 deg C; 2.) 0 deg C, 2 h 3: 85 percent / 98percent hydrazine hydrate / 0.25 h / Heating View Scheme |
2,4-diamino-5-(3-amino-4-chlorophenyl)-6-ethylpyrimidine
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) NaNO2, 5M aq. HCl; 2.) NaN3 / 1.) 0 deg C; 2.) 0 deg C, 2 h 2: 85 percent / 98percent hydrazine hydrate / 0.25 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 1.) 3M aq. HCl, aq. NaNO2 / 1.) 0 deg C; 2.) 0 deg C, 2 h 2: 95 percent / 0.5M aq. HCl / 0.08 h / Heating 3: 1.) NaNO2, 5M aq. HCl; 2.) NaN3 / 1.) 0 deg C; 2.) 0 deg C, 2 h 4: 85 percent / 98percent hydrazine hydrate / 0.25 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: NaNO2, aq. HBF4 2: 64 percent / Et3N, formamide / Ambient temperature View Scheme |
2,4-diamino-5-(4-chloro-3-nitrophenyl)-6-ethylpyrimidine
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: SnCl2*2H2O / ethanol / Heating 2: 1.) NaNO2, 5M aq. HCl; 2.) NaN3 / 1.) 0 deg C; 2.) 0 deg C, 2 h 3: 85 percent / 98percent hydrazine hydrate / 0.25 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1: SnCl2*2H2O / ethanol / Heating 2: 1.) 3M aq. HCl, aq. NaNO2 / 1.) 0 deg C; 2.) 0 deg C, 2 h 3: 95 percent / 0.5M aq. HCl / 0.08 h / Heating 4: 1.) NaNO2, 5M aq. HCl; 2.) NaN3 / 1.) 0 deg C; 2.) 0 deg C, 2 h 5: 85 percent / 98percent hydrazine hydrate / 0.25 h / Heating View Scheme |
N-[4-ethyl-5-(4-chloro-phenyl)-6-oxo-1,6-dihydro-pyrimidin-2-yl]-acetamide
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: trichlorophosphate 2: ammonia; phenol / 110 °C View Scheme |
2-(4-chloro-phenyl)-3-oxo-propionitrile
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere 1.2: 5 h / 0 - 20 °C / Inert atmosphere 2.1: sodium ethanolate / ethanol / 10 h / 80 °C 3.1: trifluoroacetic acid; acetic acid / acetonitrile / 0.17 h / 20 °C / Green chemistry 3.2: 10 h / 110 °C / 760.05 Torr / Green chemistry View Scheme |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
2,4-diamino-5-(4-chloro-3-nitrophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 50℃; for 1h; | 95% |
With sulfuric acid; nitric acid 50 deg C, 1 h; 25 deg C, 18 h; | |
With sulfuric acid; nitric acid |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
B
2,4-diamino-5-(4-chloro-3-nitrophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
A n/a B 93.8% |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
acetic anhydride
Diacetamidopyrimethamine
Conditions | Yield |
---|---|
for 2h; Heating; | 89% |
With acetic acid for 1.5h; Heating; | 57% |
pentanoic anhydride
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Pentanoic acid [5-(4-chloro-phenyl)-6-ethyl-2-pentanoylamino-pyrimidin-4-yl]-amide
Conditions | Yield |
---|---|
Heating; | 88% |
6-bromo-2-phenyl-4H-benzo[2,3-d]-1,3-oxazin-4-one
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
In acetic acid for 6h; Heating; | 84% |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
propionic acid anhydride
N-[5-(4-Chloro-phenyl)-6-ethyl-2-propionylamino-pyrimidin-4-yl]-propionamide
Conditions | Yield |
---|---|
Heating; | 83% |
2-methyl-6-bromo-4H-3,1-benzoxazine-4-one
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
In acetic acid for 6h; Heating; | 83% |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
With air; hematoporphyrin In ethanol for 7h; Irradiation; | 81% |
With air; hematoporphyrin In ethanol for 7h; Product distribution; Mechanism; Irradiation; further solvents and sensitizens; |
butanoic acid anhydride
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
N-[2-Butyrylamino-5-(4-chloro-phenyl)-6-ethyl-pyrimidin-4-yl]-butyramide
Conditions | Yield |
---|---|
Heating; | 77% |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
benzoic acid anhydride
C26H21ClN4O2
Conditions | Yield |
---|---|
Heating; | 76% |
Conditions | Yield |
---|---|
In acetone at 20℃; for 1h; Solvent; | 70% |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
2,2-dimethylpropanoic anhydride
N-[5-(4-Chloro-phenyl)-2-(2,2-dimethyl-propionylamino)-6-ethyl-pyrimidin-4-yl]-2,2-dimethyl-propionamide
Conditions | Yield |
---|---|
Heating; | 62% |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
With sodium tetrahydroborate; air; rose bengal In ethanol for 24h; Irradiation; | 39% |
With sodium tetrahydroborate; air; rose bengal In ethanol for 24h; Mechanism; Irradiation; |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
acetic anhydride
A
acetyl-pyrimethamine
B
triacetyl-pyrimethamine
Conditions | Yield |
---|---|
With pyridine Ambient temperature; | A 31.5% B 13% |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
2-amino-5-(4-chlorophenyl)-6-ethylpyrimidin-4(3H)-one
Conditions | Yield |
---|---|
With hydrogenchloride; water | |
With hydrogenchloride In water for 48h; Reflux; Inert atmosphere; |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
acetic anhydride
tetracetyl-pyrimethamine
Conditions | Yield |
---|---|
With pyridine Ambient temperature; |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
acetyl chloride
Diacetamidopyrimethamine
Conditions | Yield |
---|---|
With dmap In pyridine for 12h; Ambient temperature; |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
A
2-amino-5-(4-chlorophenyl)-6-ethylpyrimidin-4(3H)-one
B
4-amino-5-(4-chlorophenyl)-6-ethylpyrimidin-2(1H)-one
Conditions | Yield |
---|---|
With hydrogenchloride In water for 18h; Heating; | A 33 % Spectr. B 67 % Spectr. |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
A
2-amino-5-(4-chlorophenyl)-6-ethylpyrimidin-4(3H)-one hydrochloride
B
4-amino-5-(4-chlorophenyl)-6-ethylpyrimidin-2(1H)-one
Conditions | Yield |
---|---|
With hydrogenchloride In water Product distribution; boiling, 18 h; 4 deg C, 6 d; further pyrimethamine derivatives, further reagent; | A 33 % Spectr. B 7 % Spectr. |
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Conditions | Yield |
---|---|
With sodium acetate; pyridinium chlorochromate In dichloromethane for 2h; Ambient temperature; |
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%.
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. |
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