N-(4,6-Dichloro-5-nitropyrimidin-2-yl)ethanimidic acid → N-(5-amino-4,6-dichloropyrimidin-2-yl)acetamide

HRID 1760206Notes

Reaction equation

HRID 1760206 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([Cl:11])[N:5]=[C:4]([NH:12][C:13](=[O:15])[CH3:14])[N:3]=1.[H][H]>[Ni].CO>[NH2:8][C:7]1[C:6]([Cl:11])=[N:5][C:4]([NH:12][C:13](=[O:15])[CH3:14])=[N:3][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 301038N-(4,6-Dichloro-5-nitropyrimidin-2-yl)ethanimidic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 301037N-(5-amino-4,6-dichloropyrimidin-2-yl)acetamideYield 51%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

N1-(4,6-Dichloro-5-nitro-2-pyrimidinyl)acetamide (100 g, 0.40 mol) and Raney nickel (100 g, wet) were suspended in methanol (1.5 L) and stirred vigorously for 5 hours in a hydrogen atmosphere, at ordinary temperature and at normal pressure. After the nickel was filtered off, the filtrate was concentrated. The residue was crystallized from methanol/ethyl acetate, and the crystals were collected by filtration and washed with ethyl acetate, to give the title compound (44.6 g, 51%) as a brown solid.

Workup

  1. filtrationAfter the nickel was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was crystallized from methanol/ethyl acetate
  4. filtrationthe crystals were collected by filtration
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-47c26930adba4bbe9497e0826e600d8d
Source dataset
uspto-grants-2005_01
Patent number
US06841549B1

Reaction notes

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