Triethylamine → 2-amino-5-(2-(dimethylamino)ethoxy)-N-(4-methylpyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

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Reaction Conditions

Reaction Steps

To a suspension of 2-amino-5-[2-(dimethylamino)ethoxy]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (100 mg, 0.377 mmol) in NMP (667 μL) was added Et3N (46.54 mg, 64.1 μL, 0.4599 mmol) in one portion. The mixture was stirred for 10 minutes before adding TBTU (Boron Tetrafluoride Ion) (136.3 mg, 0.4245 mmol), portionwise, over 5 minutes. The mixture was allowed to stir at room temperature for 20 mins. 4-Methylpyridin-3-amine (40.77 mg, 0.377 mmol) was added and the mixture was heated to 100° C. for 4 hours. The mixture was filtered through a silica gel pad and eluted with DCM initially followed by 20/80 MeOH/DCM. The residue was further purified by preparative HPLC to provide compound I-C-3 (42% yield). LC-MS (M+H)+=356.2; 1H NMR (500 MHz, DMSO-d6) δ 9.80 (s, 1H), 9.38 (brs, 1H), 9.20 (brs, 1H), 8.82 (d, 1H), 8.50-8.43 (m, 1H), 7.66-7.6 (m, 1H), 6.62 (d, 1H), 6.50 (brs, 2H), 4.81-4.78 (m, 2H), 3.63-3.60 (m, 2H), 2.95 (s, 6H), 2.55 (s, 3H);

Provenance & Evidence