Tetrahydrofuran → 4-Bromo-5-[7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-3-yl]-thiazole-2-carbaldehyde

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Reaction Steps

Under a nitrogen atmosphere, add n-butyl lithium (1.6 M in hexanes, 0.312 mL, 0.50 mmol) to a THF solution (2.5 mL) of 3-(2,4-dibromo-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (230 mg, 0.50 mmol) at −78° C. and stir for 30 min. Add a THF (0.5 mL) solution of N-formyl morpholine (58 mg, 0.50 mmol). Stir for one hour, then store the reaction at −20° C. overnight. Warm the reaction to room temperature, dilute with ether, and quench by adding 4 N HCl (4 mL). Separate and extract the organic phase with 4 N HCl (2×4 mL). Combine the aqueous portions, treat with solid sodium bicarbonate to pH=8 to 9 and then extract with diethyl ether. Combine all the organic layers, wash with brine, dry over sodium sulfate, filter, and concentrate to a residue. Purify the crude material by flash chromatography, eluting with hexanes/dichloromethane/ethyl acetate (5/5/1) to give the title compound (154 mg). MS (APCI) m/z (81Br) 409.0 (M+1)+.

Provenance & Evidence