Sodium Carbonate → 5H-Pyrrolo3,2-dpyrimidine, 7-bromo-2-fluoro-4-(phenylmethoxy)-5-(phenylmethoxy)methyl-

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Reaction Conditions

Reaction Steps

A solution of the product from Example 11.2 (0.9 g) in dry pyridine (40 mL) was cooled in an ice bath while hydrogen fluoride-pyridine (˜65%) (15 mL) was added slowly keeping the temperature ≦10° C. The resulting solution was cooled to 0° C., tert-butyl nitrite (3 mL) was added, and the solution was stirred in the ice bath for 3 h and then poured carefully onto saturated aq NaHCO3 (500 mL) adding Na2CO3 as required to keep the solution basic. The mixture was extracted (×2) with chloroform which was dried and concentrated to dryness. Chromatography gave 4-benzyloxy-5-N-benzyloxymethyl-7-bromo-2-fluoropyrrolo[3,2-d]pyrimidine (0.63 g) as a solid. 13C NMR (CDCl3), δ 158.5 (JC,F=17 Hz), 157.5 (JC,F=213 Hz), 150.6 (JC,F=16 Hz), 136.8, 135.5, 133.9, 129.1, 128.9, 128.9, 128.5, 127.9, 114.1, 91.9, 77.9, 71.1, 70.0.

Provenance & Evidence