Diisopropylethylamine → HCID 68786687, compound

Participants

Reaction Steps

A solution of 4-chloropyrimidin-2-amine (CAS#3993-78-0, 0.200 g, 0.0015 mole), N-ethyl-N-isopropylpropan-2-amine (1.88 mL, 0.0108 mole), and tert-butyl 3-aminopropyl(methyl)carbamate (0.300 g, 0.0015 mole) in n-propanol (3 mL) was heated at 200° C. under microwave irradiation for 10 minutes. Volatiles were removed under reduced pressure and the residue was partitioned between ethyl acetate and saturated aqueous sodium carbonate. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel eluting with 97:3:trace DCM/MeOH/aq. NH4OH. Two major products were isolated. The first product to elute was the isomeric byproduct, tert-butyl 3-((2-aminopyrimidin-4-yl)(methyl)amino)propylcarbamate. The second product to elute was the desired product, tert-butyl 3-(2-aminopyrimidin-4-ylamino)propyl(methyl)carbamate (0.040 g, 9.2%). 1H NMR (300 MHz, CD3OD) δ ppm 1.43 (s, 9H), 1.79 (pentet, J=7 Hz, 2H), 2.86 (s, 3H), 3.26-3.33 (m, 4H), 5.81 (d, J=6 Hz, 1H), 7.58 (d, J=6 Hz, 1H). MS (DCl—NH3) m/z=282 (M+H)+.

Provenance & Evidence