N-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-5-nitropyrimidin-4-amine → N4-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)pyrimidine-4,5-diamine

Participants

Reaction Steps

N-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-5-nitropyrimidin-4-amine (633 mg, 0.975 mmol) was dissolved in EtOAc (25 mL) and MeOH (25 mL), and mixed with platium on carbon, sulfided (10%, wet) (127 mg, 20% w/w). The reaction mixture was applied to Parr apparatus under H2 (40 psi) for 5 h. TLC showed the reaction completed. The catalyst was filtered off and washed with MeOH. The filtrate and washings were combined and evaporated to dryness to give a white solid product (498 mg, 82%). MS (ESI): 647.5; 1H NMR (400 MHz, DMSO-d6) δ 8.95 (s, 1H), 8.18 (dd, 1H), 7.63-7.76 (m, 6H), 7.41-7.53 (m, 6H), 7.25-7.30 (m, 1H), 7.02-7.22 (m, 3H), 5.57-5.65 (m, 1H), 4.92 (broad, 2H), 4.87-4.91 (m, 1H), 2.28-2.38 (m, 1H), 1.86-1.98 (m, 2H), 1.72-1.82 (m, 1H), 1.02 (s, 9H).

Provenance & Evidence