4-Amino-6-chloro-2-(methylthio)pyrimidine Chemical Properties

Melting point:

130-132 °C (lit.)

Boiling point:

338.7±22.0 °C(Predicted)

Density 

1.395 (estimate)

refractive index 

1.6100 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

Crystalline Powder

pka

1.11±0.10(Predicted)

color 

Off-white to beige or yellow

InChIKey

ISUXMAHVLFRZQU-UHFFFAOYSA-N

CAS DataBase Reference

1005-38-5(CAS DataBase Reference)

NIST Chemistry Reference

Pyrimidine, 4-amino-6-chloro-2-(methylthio)-(1005-38-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

HS Code 

29335990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

4-Amino-6-chloro-2-(methylthio)pyrimidine Usage And Synthesis

Uses

4-Amino-6-chloro-2-(methylthio)pyrimidine is a halogenated heterocycle, a useful synthesis intermediate.

Chemical Properties

off-white to beige or yellow crystalline powder

Uses

4-Amino-6-chloro-2-(methylthio)pyrimidine is a halogenated heterocycle, a useful synthesis intermediate.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 1098, 1955 DOI: 10.1021/ja01610a006

Synthesis

General procedure for the synthesis of 4-amino-6-chloro-2-(methylthio)pyrimidine from 4,6-dichloro-2-(methylthio)pyrimidine: 1. 4,6-Dichloro-2-(methylthio)pyrimidine was added slowly in a 2L autoclave with THF and ammonia. 2. The reaction mixture was heated to 50-60°C and kept at that temperature for 3-4 hours (pressure in the reactor was maintained at 7-8 Kg/cm2). 3. The progress of the reaction was monitored by TLC. 4. After completion of the reaction, the reaction mixture was cooled to 25-35°C. 5. 5. Concentrate the reaction mixture under vacuum. 6. 6. Hexane was added and stirred at 25-35 °C for 30-45 min. 7. Collect the solid product by filtration and wash with hexane. 8. Wash the solid product with water (2 x 400 mL). 9. Dry the solid product at 25-35 °C until the moisture content (MC) is less than 2%. Yield: 352.0 g. Yield: 97.77%. HPLC purity: 99.07%. Note: For different analogs, other suitable conditions may be used, such as the use of methanol or dioxane solutions of ammonia. Example 1-2: Preparation of 4-amino-6-chloro-2-methylthiopyrimidine, step 6.1.

References

[1] Patent: WO2011/97594, 2011, A2. Location in patent: Page/Page column 100-101
[2] Chemistry - A European Journal, 1999, vol. 5, # 12, p. 3450 - 3458
[3] Patent: WO2007/141571, 2007, A2. Location in patent: Page/Page column 25
[4] American Chemical Journal, 1904, vol. 32, p. 353
[5] Patent: US2005/288502, 2005, A1. Location in patent: Page/Page column 20

4-Amino-6-chloro-2-(methylthio)pyrimidine(1005-38-5)Related Product Information

• Cyclamic acid
• Glycine
• Bis(2-ethylhexyl)amine
• ISOMETHIOZIN
• 4-Aminopyrimidine
• Molasses
• ALTRENOGEST
• 4-Amino-6-chloropyrimidine
• Diethylaminosulfur trifluoride
• Triethanolamine
• 6-Aminocaproic acid
• N-Ethylmethylamine
• Pyrimidine
• Triethylamine
• Tris(hydroxymethyl)aminomethane
• Difluorochloromethane
• 2-Aminobenzylchloride
• WY-14643