Sodium Iodide → HCID 24954477, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 3-(6-chloro-2-(2-chlorophenyl)pyrimidin-4-yl)azetidine-1-carboxylate (280 mg, 0.74 mmol), 5-methyl-1H-pyrazol-3-amine (86 mg, 0.88 mmol), DIPEA (124 mg, 0.96 mmol) and sodium iodide (122 mg, 0.81 mmol) in DMF (5 mL) was heated at 120° C. overnight. The reaction mixture was concentrated and the residue partitioned between EtOAc and brine. After a further extraction with EtOAc, the combined organics were dried (MgSO4), filtered and concentrated. Purification was achieved by column chromatography (eluting with petroleum ether/ethyl acetate, 1/1). The residue was dissolved in TFA (1 mL) and DCM (3 mL) and stirred for 45 min and then concentrated. Purification by Gilson preparatory HPLC gave the azetidine as a white solid (32 mg, 13%). MS (ES+) m/e=341. 1H NMR: (DMSO) 2.23 (3H, s), 4.05-4.28 (5H, m), 6.25 (1H, s), 7.11 (1H, s), 7.43-7.65 (3H, m), 7.78 (1H, d), 8.97 (1H, s), 9.61 (1H, s), 10.47 (1H, s).

Provenance & Evidence