tert-Butyl 6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl(methyl)carbamate → tert-Butyl 6-(4-amino-2-fluorophenoxy)pyrimidin-4-yl(methyl)carbamate

HRID 1670198Notes

Reaction equation

HRID 1670198 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:6]=1>O=[Pt]=O.CCO.CO>[NH2:24][C:22]1[CH:21]=[CH:20][C:3]([O:4][C:5]2[N:10]=[CH:9][N:8]=[C:7]([N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:6]=2)=[C:2]([F:1])[CH:23]=1

Participants

4

Reactant 1

HCID 59852957tert-Butyl 6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl(methyl)carbamate

Product 1

HCID 59853009tert-Butyl 6-(4-amino-2-fluorophenoxy)pyrimidin-4-yl(methyl)carbamateYield 75%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

A mixture of tert-butyl 6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl(methyl)carbamate in 1:1 EtOH/MeOH (2 mL) was treated with PtO2 (10 mg) and the reaction mixture was stirred under a blanket of H2 (from a latex balloon) for 2 h. The reaction mixture was filtered and concentrated to give the desired product (30 mg, 75%) as a light brown solid. MS (ESI+) m/z 365.13 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c45932d8ae6c470684d77553523e099a
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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