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

HRID 882114Notes

Reaction equation

HRID 882114 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]3[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.C(Cl)Cl.[Pt]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[C:11]3[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 117703162ethyl 4-(3-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Product 1

HCID 71598790ethyl 4-(3-aminophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  1. filtrationThe mixture was filtered with celite
  2. washwashed with DCM and MeOH solution

Sources & evidence

ORD record
ord-2ee9c601e6274f1cbf859521da32983b
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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