Diisopropylethylamine → HCID 86668108, compound

Participants

Reaction Steps

To a solution of 2,4-dichloro-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (Preparation of R, 1.1 g, 4.163 mmol) in acetonitrile (40 mL) was added diisopropylethylamine (0.807 g, 6.245 mmol) followed by 2-(4-aminobutoxy)-4-nitrobenzonitrile (Preparation O, 1.174 g, 4.99 mmol) at room temperature. The reaction mixture was stirred at rt for 18 h. The solvent was removed under reduced pressure and the residue was taken up in dichloromethane (10 mL) and silica (2 g). The resultant slurry of the compound on silica was subjected to flash chromatography using a Teledyne Isco instrument (12 g RediSep silica column, with 50% ethyl acetate in pet-ether) to get 2-(4-(2-chloro-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ylamino)butoxy)-4-nitrobenzonitrile (0.9 g, 47%) as a light yellow solid. LC-MS (M+H)+=464.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.08 (1H, d, J=8.4 Hz), 7.98 (1H, s), 7.91 (1H, d, J=8.8 Hz), 7.57 (1H, m), 7.32-7.13 (5H, m), 4.39-4.35 (2H, t, J=6.4 Hz), 4.19-4.15 (1H, t, J=8.0 Hz), 3.46-3.33 (2H, m), 2.85-2.75 (1H, m), 2.60-2.50 (2H, m), 1.99-1.00 (1H, m), 1.88-1.75 (4H, m).

Provenance & Evidence