Dimethylamine → HCID 10159659, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[7-chloro-2-(3-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (60 mg, 0.14 mmol) in N,N-dimethylformamide (10 mL) was added dimethylamine (7 mL 40% in water). The solution was heated in a steal bomb at 100° C. for 3 days. The bomb was cooled to room temperature and ethyl acetate was added to the reaction mixture. The organics were washed with water, brine and dried over magnesium sulfate. Filtration and concentration followed by purification with flash chromatography (95:5-dichloromethane: methanol) gave 3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(3-methoxyphenyl)-N,N-dimethylpyrazolo[1,5-a]pyridin-7-amine (43 mg, 70%) as a yellow foam. 1H NMR (CDCl3) δ 8.11 (d, 1H), 7.95 (s, 1H), 7.35–7.30 (m, 2H), 7.24–7.21 (m, 2H), 6.97 (dd, 1H), 6.36 (d, 1H), 6.32 (d, 1H), 5.40 (broad s, 1H), 4.37 (m, 1H), 3.80 (s, 3H), 3.12 (s, 6H), 2.11–2.06 (m, 2H), 1.77–1.56 (m, 6H); MS m/z 429.

Provenance & Evidence