Sodium Hydroxide → 2-chloro-4-cyclopropyl-5-fluoroPyrimidine

Participants

Reaction Conditions

Reaction Steps

In a 20 mL glass microwave tube 2,4-dichloro-5-fluoropyrimidine (500 mg, 2.99 mmol) and Amphos (53.0 mg, 0.075 mmol) were treated with 0.5 M cyclopropylzinc(II) bromide (7786 μL, 3.89 mmol) via syringe under an atmosphere of argon. The solution was then heated in the microwave at 70° C. for 20 min. The mixture was treated with 1N NaOH and extracted with EtOAc (25 mL), dried over MgSO4, filtered and concentrated. Purification with flash chromatography (eluting with 100% DCM) afforded 2-chloro-4-cyclopropyl-5-fluoropyrimidine (263 mg, 51%) as a pale yellow viscous oil. MS (ESI, pos. ion) m/z: 173.0 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.21-8.28 (1H, m), 2.24-2.34 (1H, m), 1.27-1.34 (2H, m), 1.17-1.27 (2H, m).

Provenance & Evidence