Diisopropylethylamine → {2-[5-(4-Fluorophenylcarbamoyl)-2-methylsulfanylpyrimidin-4-ylamino]-ethyl}carbamic acid tert-butyl ester

Participants

Reaction Steps

tert-Butyl N-(2-aminoethyl)carbamate (0.500 g, 3.12 mmol) and DIPEA (0.83 mL, 4.68 mmol, 1.5 eq) was added to a solution of 4-chloro-2-methylsulfanylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (0.929 g, 3.12 mmol) in DMF (5.0 ml) and stirred under N2 overnight. The reaction mixture was diluted with ethyl acetate (50 mL) and washed twice with water (50 mL). Upon precipitation of product out of the organic layer of the mixture, the white solid was filtered, and recrystallized from hot ethyl acetate to yield 1.06 g (80%) of the titled product as a white solid. 1H NMR: (d6-DMSO) δ 10.21 (s, 1H), 8.56 (s, 1H), 7.64 (m, 2H), 7.16 (m, 2H), 6.92 (t, 1H), 3.48 (m, 2H), 3.30 (s, 3H), 3.11 (m, 2H), 1.31 (s, 9H); HPLC: Rt=4.32 min; MS (ESI): m/z 419.97 (M−H)−.

Provenance & Evidence