Dimethylamine → {1-[1-(5-Iodo-pyrimidin-2-yl)-cyclopropylcarbamoyl]-cyclopropyl}-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of [1-(1-carbamimidoyl-cyclopropylcarbamoyl)-cyclopropyl]-carbamic acid tert-butyl ester hydrochloride (1.65 g, 5.2 mmol) in anhydrous EtOH (21 mL), was added 3-dimethylamino-2-iodo-propenal (1.3 g, 5.63 mmol) and 2M dimethylamine in THF (3.36 mL, 6.7 mmol). The vessel was capped and heated at 70° C. overnight. After 18 h, EtOH was removed in-vacuo and the dark orange residue was triturated with 5% iPrOH in EtOAc. A yellow solid was filtered off. The filtrate was concentrated in vacuo and purified by normal phase flash chromatography on silica gel (0→5% MeOH/CH2Cl2) to yield a black oil. This oil was treated with Et2O to precipitate a white solid. The solid was filtered off and the filtrate was reprocessed to give another crop of slightly darker solids. A total of 426 mg of {1-[1-(5-iodo-pyrimidin-2-yl)-cyclopropylcarbamoyl]-cyclopropyl}-carbamic acid tert-butyl ester was isolated, m/z 445.5 [M+H]+.

Provenance & Evidence