5-Pyrimidinamine, 2-chloro-4-methyl- (9CI) Chemical Properties

Melting point:

93.5℃

Boiling point:

309.4±22.0 °C(Predicted)

Density 

1.349±0.06 g/cm3(Predicted)

storage temp. 

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

pka

0.36±0.29(Predicted)

Appearance

Off-white to light yellow Solid

InChI

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

InChIKey

RZAKVHVZRSQZEQ-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2933599590

5-Pyrimidinamine, 2-chloro-4-methyl- (9CI) Usage And Synthesis

Synthesis

The general procedure for the synthesis of 5-amino-2-chloro-4-methylpyrimidine from 2,4-dichloro-5-nitro-6-methylpyrimidine was as follows: to a stirred methanol (100 mL) solution of 2,4-dichloro-6-methyl-5-nitropyrimidine (10 g, 48.1 mmol) and ammonium chloride (25.7 g, 481 mmol) under nitrogen protection was added in batches zinc powder ( 31.4 g, 481 mmol). The reaction mixture was stirred at 70 °C for 50 hours. After completion of the reaction, the mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol, 30:1). All fractions containing the target product were collected and detected by thin layer chromatography (unfolding agent: ethyl acetate/petroleum ether, 1:1, Rf=0.6), combined and concentrated to give 2-chloro-4-methylpyrimidin-5-amine (2 g, 13.93 mmol, 29.0% yield) as a light yellow solid. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.95 (s, 1H), 3.66 (s, 2H), 2.88 (s, 3H); ESI-MS m/z: 144.2 ([M+H]+).

References

[1] Patent: WO2016/37578, 2016, A1. Location in patent: Page/Page column 138
[2] Chemische Berichte, 1901, vol. 34, p. 1242
[3] Yakugaku Zasshi, 1942, vol. 62, p. 315,333; dtsch. Ref. S. 95, 106
[4] Chem.Abstr., 1951, p. 5150
[5] Patent: EP2100894, 2009, A1. Location in patent: Page/Page column 20

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