[4-(6-Chloro-5-nitro-pyrimidin-4-ylamino)-phenyl]-acetic acid ethyl ester → [4-(5-Amino-6-chloro-pyrimidin-4-ylamino)-phenyl]acetic acid ethyl ester

HRID 1661036Notes

Reaction equation

HRID 1661036 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[C:18]([N+:19]([O-])=O)=[C:17]([Cl:22])[N:16]=[CH:15][N:14]=2)=[CH:8][CH:7]=1)[CH3:2]>C1COCC1.[Ni]>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13]2[C:18]([NH2:19])=[C:17]([Cl:22])[N:16]=[CH:15][N:14]=2)=[CH:10][CH:11]=1)[CH3:2]

Participants

4

Reactant 1

HCID 86625829[4-(6-Chloro-5-nitro-pyrimidin-4-ylamino)-phenyl]-acetic acid ethyl ester

Product 1

HCID 86625828[4-(5-Amino-6-chloro-pyrimidin-4-ylamino)-phenyl]acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [4-(6-chloro-5-nitro-pyrimidin-4-ylamino)-phenyl]-acetic acid ethyl ester (0.400 g, 1.19 mmol) and Raney Ni (˜0.100 g) in THF (10 mL) is stirred for 20.5 h at rt, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of celite and concentrated. Purification of the residue by silica gel column chromatography (Hexane/EtOAc, 70:30) provides the title compound as a yellow solid: ES-MS: 307.1 [M+H]+; single peak at tR=3.81 min (System 1); Rf=0.06 (Hexane/EtOAc, 70:30).

Workup

  1. filtrationThe reaction mixture is filtered through a pad of celite and
  2. concentrationconcentrated
  3. customPurification of the residue by silica gel column chromatography (Hexane/EtOAc, 70:30)

Sources & evidence

ORD record
ord-03a9ca05078541318ee63d3fa6e87d65
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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