Diisopropylethylamine → [4-({2-[(Isoquinolin-1-ylmethyl)-amino]-5-nitro-pyrimidin-4-ylamino}-methyl)-cyclohexyl]-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a solution of isoquinolin-1-yl-methylamine (1.32 g, 8.35 mmol) and diisopropylethylamine (2.7 mL, 15.5 mmol) in DMF (20 mL) was added {4-[(2-chloro-5-nitro-pyrimidin-4-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester (1.5 g, 3.89 mmol). The reaction mixture was stirred at room temperature for 10 min. The solvent was removed and the resulting residue was diluted with a mixture of ethyl acetate (350 mL) and CH2Cl2 (100 mL). The solution was then washed with 1M Na2CO3 and water. The organic phase was dried over Na2SO4 and concentrated. The resulting solid was treated with ethyl acetate (poor solubility of the product in ethyl acetate) and the un-dissolved solid was filtered through a Buchner funnel. The white solid was dried in vacuo to yield 1.64 g of [4-({2-[(isoquinolin-1-ylmethyl)-amino]-5-nitro-pyrimidin-4-ylamino}-methyl)-cyclohexyl]-carbamic acid tert-butyl ester.

Provenance & Evidence