Tert-butyl 6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-ylcarbamate → Tert-butyl 6-(4-amino-2-fluorophenoxy)pyrimidin-4-ylcarbamate

HRID 1670195Notes

Reaction equation

HRID 1670195 reaction equation
[F:1][C:2]1[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:6]=1.[H][H]>CO.O=[Pt]=O>[NH2:23][C:21]1[CH:20]=[CH:19][C:3]([O:4][C:5]2[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:6]=2)=[C:2]([F:1])[CH:22]=1

Participants

5

Reactant 2

HCID 59852921Tert-butyl 6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-ylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 59853037Tert-butyl 6-(4-amino-2-fluorophenoxy)pyrimidin-4-ylcarbamateYield 81%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-ylcarbamate (11 mg, 0.031 mmol) in MeOH (2 mL) was treated with PtO2 and the reaction mixture was stirred under a blanket of hydrogen (from a latex balloon) for 2 h. The catalyst was filtered off and the filtrate concentrated to give tert-butyl 6-(4-amino-2-fluorophenoxy)pyrimidin-4-ylcarbamate (8 mg, 81%). 1H NMR (DMSO-d6) δ 10.62 (s, 1H), 8.43 (d, 1H, J=2.5 Hz), 8.36 (dd, 1H, J=9.8, 2.5 Hz), 8.36 (dd, 1H, J=9.8, 2.5 Hz), 8.20-8.17 (m, 1H), 7.71 (dd, 1H, J=8.8, 8.8 Hz), 7.49 (s, 1H), 1.48 (s, 9H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-11a5f201c4e141f9a1f5bbe07af0ceb5
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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