Triethylamine → 1H-benzo[d][1,2,3]triazol-1-yl 2-amino-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

Triethylamine (994.9 mg, 1.370 mL, 9.832 mmol) was added to a suspension of 2-amino-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid 5a (2.2 g, 8.938 mmol) in chloroform (22 mL). TBTU (2.870 g, 8.938 mmol) was added to the solution and the reaction mixture was heated at 50° C. for 20 min, during which time a yellow precipitate formed. The reaction mixture was cooled to ambient temperature. The precipitate was isolated by filtration and washed with chloroform to leave the product (benzotriazol-1-yl 2-amino-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate) 6a as an off-white solid (2.8 g, 86% yield).). LC-MS (M+H)+ 364.0; 1H NMR (500 MHz, DMSO-d6) δ 9.40-9.28 (m, 1H), 8.19 (dt, J=8.5, 0.9 Hz, 1H), 7.80 (dt, J=8.4, 0.9 Hz, 1H), 7.72-7.63 (m, 2H), 7.55 (m, J=8.5, 6.9, 1.0 Hz, 1H), 7.13 (s, 2H).

Provenance & Evidence