Sodium Carbonate → {2,6-Dimethyl-4-[(4-methyl-2-phenyl-pyrimidin-5-ylmethyl)-amino]-phenyl}-carbamic acid propyl ester

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Reaction Conditions

Reaction Steps

(4-Amino-2,6-dimethyl-phenyl)-carbamic acid propyl ester (22 mg) and 4-methyl-2-phenyl-5-pyrimidinecarbaldehyde (20 mg) were dissolved in methanol (0.5 mL) and heated to 170° C. for 10 minutes in a sealed microwave process vial. Sodium cyanoborohydride (2 M in methanol, 250 uL) and acetic acid (100 uL) were added and the reaction mixture was heated to 50° C. for 2 hours. Aqueous sodium carbonate (10%, 1 mL) was added, the product was extracted with ethyl acetate (2×1 mL), and the combined organic phases were concentrated in vacuo. The crude product was redissolved in dimethyl sulfoxide (0.5 mL) of which 0.25 mL was subjected to preparative LC-MS purification to furnish 6.6 mg (33% yield) of the title compound as an oil. LC-MS (m/z) 405 (MH+); tR=3.12, (UV, ELSD) 84%, 99%.

Provenance & Evidence