Hydrochloric Acid → 6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl 6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinate (1.0 g, 2.4 mmol) in 2-propanol (60 mL) were added LiOH (0.29 g, 5.0 eq) and water (12 mL) and the resulting mixture was stirred at 60° C. for 1 h. After cooling to room temperature, the reaction mixture was treated with 1 N HCl (12.24 mL, 5 eq) and concentrated in vacuo which gave 6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid as a light yellow solid (1.40 g) in 95% yield as the LiCl (5 equiv) co-salt and was used for the next reaction without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.30 (br s, 1H), 11.24 (br s, 1H), 9.03 (s, 1H), 8.88 (d, J=2.2 Hz, 1H), 8.31 (dd, J=8.7, 2.2 Hz, 1H), 8.11 (d, J=8.7 Hz, 1H), 6.81 (s, 1H), 4.79 (m, 1H), 3.06 (s, 6H), 2.41 (m, 2H), 2.02 (m, 4H), 1.67 (m, 2H); MS m/z 395.4 (M+H)+.

Provenance & Evidence