Hydrochloric Acid → HCID 10400931, compound

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Reaction Steps

A solution of 2-(diethoxymethyl)-3-[2-(methylthio)pyrimidin-4-yl]pyrazolo[1,5-a]pyridine (1.3 g, 3.8 mmol) in tetrahydrofuran (20 mL) was treated with aqueous hydrochloric acid (10 mL 4 M), the resultant solution was stirred for 18 h. The solvents were removed in vacuo and the residue was taken up in dichloromethane and the pH adjusted to >7 with 1N aqueous sodium hydroxide. The organic layer was washed with brine. The aqueous layer was extracted with dichloromethane and the combined organics were dried over sodium sulfate. Filtration and concentration followed flash chromatography on silica gel (1:1 to 1:2 hexane-ethyl acetate) provided 3-[2-(Methylthio)pyrimidin-4-yl]pyrazolo[1,5-a]pyridine-2-carbaldehyde (804 mg, 790%) as a yellow solid. 1H NMR (CDCl3) δ 10.42 (s, 1H), 8.61–8.58 (m, 3H), 7.92 (d, 1H), 7.44 (m, 1H), 7.12 (m, 1H), 2.65 (s, 3H); MS m/z 271 (M+1).

Provenance & Evidence