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0 °C

5-bromo-4-chlorothieno[2,3-d]pyrimidine (750 mg, 3.0 mmol) was partially dissolved in anh. THF (8 mL), cooled to 0° C. and treated in portions with a 2M THF solution of i-PrMgCl (2.0 mL, 4.0 mmol). After 20 minutes, this solution was treated dropwise with methylmethanethiosulfonate (460 μl, 570 mg, 4.5 mmol). The cooling bath was removed and the mixture was stirred for 4 hours at 25° C. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic phase was washed with water, brine, dried (Na2SO4) and evaporated to give 830 mg crude product-ca 80 percent pure by GC. The material was purified by recrystallization from hot heptane to give 350 mg (45 percent) yield of tan crystals.

1. customThe cooling bath was removed
2. customThe reaction was quenched with saturated aqueous NH4Cl
3. extractionextracted with EtOAc
4. washThe organic phase was washed with water, brine
5. dry with materialdried (Na2SO4)
6. customevaporated