Hydrochloric Acid → 6-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidine

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Reaction Conditions

Reaction Steps

5-amino-4-methylpyrimidine (5 g, 45 mmol) was dissolved in 200 mL THF and cooled to −20° C. A solution of n-BuLi (112.5 mmol) was added over 10 minutes and the solution was kept at −20° C. for 30 min, then warmed to room temp and stirred for 3 h. It was then cooled to −40° C. and to it was added methyl-2-fluorobenzoate (1.75 mL, 13.7 mmol) and the solution stirred at −40° C. for 30 min and then warmed to room temp for 1 h. 50 mL of methanol was then added over 5 min, followed by 6N aq HCl. The solution was stirred for 18 h at room temp. It was then neutralized with NaHCO3 to pH 8 and then diluted with ethyl acetate and water. The organics were washed with water three times and then brine and dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash chromatography using 10% methanol/DCM. 1.5 g of product was isolated as a yellow solid (16%). 1H-NMR: (d6-DMSO, 400 MHz) δ 12.22 (s, 1H), 8.86 (s, 1H), 8.83 (s, 1H), 7.98(dt, 1H), 7.46 (m, 1H), 7.38 (m, 2H), 7.02(s, 1H) LC/MS: calculated for C12H8FN3: 213.2; found 214.10 (M+H)+.

Provenance & Evidence