Acetic Acid → HCID 89445309, compound

Participants

Reaction Steps

The 6,8-dimethyl-1H-pyrazolo[3′,4′:4,5]thieno[2,3-b]pyridin-3-amine (75 mg, 0.34 mmol) was stirred in DCE (3.4 mL). To this solution was added acetone (0.08 mL, 1.03 mmol) and acetic acid (0.060 mL, 1.03 mmol). The mixture was stirred 15 minutes, then NaBH(AcO)3 (150 mg, 0.70 mmol) was added. The resulting slurry was stirred about 2 hrs. LC/MS indicates the reaction is complete. The reaction was diluted with DCM (15 mL) and quenched with aqueous 2N NaOH. The aqueous layer was separated and extracted with DCM. The combined organic layers were dried over Na2SO4, and concentrated under vacuum to give a crude residue. The residue was purified by trituration with MeOH to give the pure product, 30 mg, (33%), as a light tan solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.09 (s, 1H), 5.65 (bs, 1H), 3.61 (bs, 1H), 2.63 (s, 3H), 2.50 (s, 3H), 1.17 (d, J=6.32, 6H). LC/MS: RT=0.55 min., m/z=261.0 [M+H]+.

Provenance & Evidence