Cyclobutanone → HCID 89924012, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-iodopyrimidine (12.5 g, 43.88 mmol) was suspended in dry toluene (250 mL), then cooled to −78° C. under N2. n-Butyllithium (2.5M solution in hexanes, 20 mL) was added dropwise, and the reaction mixture was aged for 20 minutes prior to dropwise addition of a solution of cyclobutanone (3.75 g, 53.5 mmol) in dry toluene (10 mL). The reaction mixture was stirred at −78° C. for 45 minutes, then allowed to warm to room temperature. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (3×300 mL). The combined organic extracts were dried over MgSO4 and the solvent removed under reduced pressure. The resulting brown oil was purified by chromatography on silica (Biotage, 340 g cartridge), eluting with a gradient of 0-100% ethyl acetate in heptanes, to afford the title compound (4.76 g) as a bright yellow solid. δH (500 MHz, CD3OD) 8.80 (s, 2H), 2.57 (dddd, J 11.2, 5.2, 4.4, 2.5 Hz, 2H), 2.32-2.23 (m, 2H), 1.93-1.76 (m, 2H). Method C HPLC-MS: MH+ m/z 230, RT 1.06 minutes.

Provenance & Evidence