Pyrimidine → Methyl 3-[cyclopentyl(2-chloro-5-nitropyrimidin-4-yl)amino]propanoate

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Reaction Steps

Methyl 3-(cyclopentylamino)propanoate (0.838 g, 0.005 mol, 1 eq) and K2CO3 (0.676 g, 0.005 mol, 1 eq) were added to acetone (5 mL) and the resulting mixture cooled to 0° C. before the dropwise addition of 2,4-dichloro-5-nitropyrimidine (1.04 g, 0.0055 mol, 1.1 eq). The reaction mixture (RM) was warmed to rt and stirring continued for an additional 16 h before the addition of a further 0.12 eq of the pyrimidine. Stirring continued for a further 3 h. The RM was evaporated under reduced pressure and the product extracted using EtOAc/H2O. The organic extracts were washed with sat NaCl, dried (MgSO4) and evaporated under reduced pressure to give the product as a brown oily residue (1.04 g, 65%); MS+ve: 329.2; Rt=3.78 min (Analytical—1).

Provenance & Evidence