2,4-Dibenzyloxy-6-(2-dimethylaminovinyl)-5-nitropyrimidine → 5H-Pyrrolo3,2-dpyrimidine, 2,4-bis(phenylmethoxy)-

Participants

Reaction Steps

To a suspension of 2,4-Bis-O-Benzyl-5-nitro-6-β-dimethylaminovinyl pyrimidine 14 (2 g, 4.9 mmol) in AcOH (40 ml), Zn (4 g) was added in lot of 2 g with an interval of 4 hrs. The reaction mixture was stirred overnight at room temperature during which a dark yellow suspension became pale yellow suspension. The reaction mixture was filtered and the filtrate concentrated in vacuo to obtain syrup which was dissolved in CH2Cl2 then washed with saturated aq. NaHCO3 followed by brine. The organic phase was dried over MgSO4 and loaded on silica. The product 15 was purified using column chromatography eluting with 4:1 and 1:1 hexanes/EtOAc to obtain product as pale-yellow solid (1.45 g, 90%). Rf 0.3 in 1:3 hexanes/EtOAc. 1H NMR (400 MHz, CDCl3): δ 5.47 (s, 2H), 5.54 (s, 1H), 6.50-6.51 (dd, 1H, J=1.84, 2.28), 7.29-7.38 (m, 7H), 7.43-7.45 (m, 2H), 7.52-7.53 (m, 2H), 8.41 (br s, 1H, NH). 13C NMR (400 MHz, CDCl3): δ 68.3, 69.0, 102.6, 111.9, 127.8, 128.3, 128.4, 128.5, 128.6, 128.7, 128.8, 136.1, 137.3, 151.8, 156.79, 159.7. FAB-MS for C20H17N3O2 calculated [M+H]+ 332.1394. found 332.1398.

Provenance & Evidence