Methylhydrazine → 2-Methylsulfanyl-pyrimidine-4-carboxylic acid N-methyl-hydrazide

Participants

Reaction Conditions

Reaction Steps

To a −78° C. stirred solution of methyl hydrazine (17 mL, 318 mmol) in CH2Cl2 (500 mL) is added dropwise a solution of 2-methylsulfanyl-pyrimidine-4-carbonyl chloride (20 g, 106 mmol) in CH2Cl2 (500 mL). The reaction mixture is stirred for 2 hours at −78° C. and then slowly warmed to room temperature. The reaction mixture is concentrated under reduced pressure to give a purple oil. Purification over silica (EtOAc/hexanes 1:1) affords 6.98 g (33% yield) of the desired compound. 1H NMR (300 MHz, CDCl3) δ 8.69-8.64 (m, 1H), 7.35-7.08 (m, 1H), 3.40 (s, 3H), 3.36 (s, 2H), 2.59 (s, 3H); ESI/MS: 199.1 (M+H).

Provenance & Evidence