4-Amino-6-chloro-2-methylpyrimidine Chemical Properties

Melting point:

189 °C

Boiling point:

269.2±20.0 °C(Predicted)

Density 

1.349±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

solid

pka

3.57±0.10(Predicted)

color 

White

InChI

InChI=1S/C5H6ClN3/c1-3-8-4(6)2-5(7)9-3/h2H,1H3,(H2,7,8,9)

InChIKey

SSAYHQQUDKQNAC-UHFFFAOYSA-N

SMILES

C1(C)=NC(Cl)=CC(N)=N1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2933599590

4-Amino-6-chloro-2-methylpyrimidine Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-methyl-4-amino-6-chloropyrimidine from 4,6-dichloro-2-methylpyrimidine: 4,6-dichloro-2-methylpyrimidine (50 g, 0.31 mol) and a methanol solution of ammonia (0.5 L) were added to a 1 L triple-necked flask, and the reaction was stirred for 5 h at 50 °C. After completion of the reaction, the reaction mixture was cooled to 0 °C. Subsequently, filtration was carried out at room temperature and the filter cake was washed with petroleum ether (100 ml). Finally, the product was dried under reduced pressure to afford 2-methyl-4-amino-6-chloropyrimidine (40.9 g, yield: 92%) as a white solid.

References

[1] Patent: CN106478519, 2017, A. Location in patent: Paragraph 0024-0027; 0033-0035; 0041-0044; 0053-0056
[2] Journal of Organic Chemistry, 2016, vol. 81, # 9, p. 3780 - 3789
[3] Tetrahedron Letters, 2009, vol. 50, # 41, p. 5729 - 5732
[4] Patent: US2015/133474, 2015, A1. Location in patent: Paragraph 0023-0024
[5] Patent: WO2015/73281, 2015, A1. Location in patent: Page/Page column 6

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