Sodium Hydroxide → 5-Amino-2-[3-(1-adamantyl)-4-benzyloxyphenyl]pyrimidine

Participants

Reaction Steps

A solution of 2-[3-(1-adamantyl)-4-benzyloxyphenyl]-5-nitropyrimidine (163 mg, 0.37 mmol) and SnCl2.2H2O (418 mg, 1.85 mmol) in anhydrous EtOH (1.7 mL) was heated at 90° C. (oil-bath) for 3.3 h, cooled to room temperature and diluted with H2O (2 mL). After adjustment of the pH to 7-8 by addition of 2 N NaOH (1.6 mL) and 5% NaHCO3 (3 mL), the resulting mixture was stirred for 40 min and extracted with EtOAc (3×30 mL). The extract was washed (brine) and dried. After solvent removal at reduced pressure, the residue was chromatographed (25% EtOAc/hexane) to give 53 mg (35%) of 5-amino-2-[3′-(1-adamantyl)-4′-benzyloxyphenyl]pyrimidine as a light-purple solid, mp 216-219° C. IR 3424, 2900, 1182 cm−1; 1H NMR (CDCl3) 1.76 (bs, 6H, AdCH2), 2.08 (bs, 3H, AdCH), 2.24 (m, 6H, AdCH2), 3.74 (bs, 2H, NH2), 5.21 (s, 2H, C6H5CH2), 7.04 (d, J=8.7 Hz, 1H, 5′-ArH), 7.34-7.56 (m, 5H, C6H5), 8.13 (dd, J=8.7 Hz, 2.4 Hz, 1H, 6′-ArH), 8.28 (d, J=2.4 Hz, 1H, 2′-ArH), 8.43 ppm (s, 2H, 4-ArH, 6-ArH). HRMS calcd C27H29N3O [M+H]+ 412.2389. found 412.2391.

Provenance & Evidence