Hydrochloric Acid → 5-Bromo-2-chloropyrimidin-4-ol

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Reaction Steps

5-Bromo-2,4-dichloro-pyrimidine (5.0 g, 22 mmol) was stirred in THF (10 mL) with 1N NaOH (30 mL) at r.t. for 3 h. The solution was made slightly acidic with 1N HCl and was extracted with CHCl3. Organics were dried (MgSO4) and concentrated in vacuo. Precipitation from 20% CHCl3/hexanes and collection by filtration gave 2.92 g (64%) of 5-bromo-2-chloro-3H-pyrimidin-4-one as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 13.33 (br s, 1H), 8.35 (s, 1H). MS (ES) [m+H] calc'd for C4H2N2OBrCl, 209, 211, 213; found 209, 211, 213.

Provenance & Evidence