2-Bromopropane → 4-Chloro-5-iodo-7-(propan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

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Reaction Steps

4-Chloro-5-iodopyrrolo[2,3-d]pyrimidine (10.0 g, see Example 17) was added in portions with stirring under nitrogen at 0° C. to a suspension of sodium hydride (1.6 g of a 60% dispersion in mineral oil) in N,N-dimethylformamide (250 ml). When the addition was complete the mixture was allowed to warm up to ambient temperature and when no more gas evolution was observed, a solution of isopropyl bromide (34.0 ml) in N,N-dimethylformamide (20 ml) was added dropwise. The mixture was stirred at ambient temperature overnight then quenched by the dropwise addition of water (300 ml) with external ice-cooling. The mixture was then washed with ethyl acetate (3×300 ml), the combined organic layers were washed with water, dried, filtered and evaporated to give 4-chloro-5-iodo-7-isopropylpyrrolo-[2,3-d]pyrimidine as a yellow solid, m.p. 116-118° C. The structure was confirmed by 1H nmr.

Provenance & Evidence