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

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.

1. additionWhen the addition
2. customthen quenched by the dropwise addition of water (300 ml) with external ice-
3. temperaturecooling
4. washThe mixture was then washed with ethyl acetate (3×300 ml)
5. washthe combined organic layers were washed with water
6. customdried
7. filtrationfiltered
8. customevaporated

ORD record

ord-dcd60a91bc444b4da7c0aa11ae007259

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06001839