ethyl 4-(3-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate → ethyl 4-(3-aminophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

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Reaction Steps

To ethyl 4-(3-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (7.60 g, 24.3 mmol) in methanol (40.6 mL) and CH2Cl2 (40.6 mL) was added 3% Pt on carbon doped with 0.6% V (4.75 g, 0.730 mmol) and the mixture was stirred under a H2 balloon overnight. The mixture was filtered with celite and washed with DCM and MeOH solution to give ethyl 4-(3-aminophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate after removal of solvent. LRMS (ESI) calc'd for C15H15N4O2 [M+H]+: 283, found 283. 1H NMR (600 MHz, DMSO-D6) δ 12.85 (s, 1H), 8.85 (s, 1H), 8.22 (s, 1H), 7.09 (t, J=7.8 Hz, 1H), 6.90 (s, 1H), 6.71 (d, J=7.2 Hz, 1H), 6.67 (d, J 6.0 Hz, 1H), 5.17 (s, 2H, NH2), 3.86 (q, J=7.2 Hz, 2H), 0.84 (t, J=7.2 Hz, 3H).

Provenance & Evidence