Formamide → 1-(2-Hydroxy-2-phenylethyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

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Reaction Conditions

Reaction Steps

A suspension of 5 (2.75 g, 10 mmol) in formamide (10 g, 333 mmol) was heated at 190° C. for 8 h and then poured in H2O (300 mL). The crude was filtered and purified by dissolving in 2M NaOH (100 mL), boiling with coal, followed by precipitation with glacial acetic acid. The solid was filtered and recrystallized from absolute ethanol to give 10 (1.79 g, 70%) as a white solid: mp 270-271° C. 1H NMR: δ 4.25-4.55 (m, 2H, CH2), 5.05-5.15 (m, 1H, CHO), 5.65 (d, 1H, OH, disappears with D2O), 7.25-7.45 (m, 5H Ar), 8.05 (s, 1H, H-3), 8.10 (s, 1H, H-6), 12.15 (br s, 1H, NH, disappears with D2O). IR cm−1: 3400 (NH), 3245-2500 (OH), 1740 (CO). Anal. (C13H12N4O2) C, H, N.

Provenance & Evidence