Ethyl Acetate → 4,6-dichloro-2-ethylpyrimidin-5-amine

HRID 345425Notes

Reaction equation

HRID 345425 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([Cl:11])[N:5]=[C:4]([CH2:12][CH3:13])[N:3]=1.CCOC(C)=O>CO.[Ni]>[NH2:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([CH2:12][CH3:13])=[N:5][C:6]=1[Cl:11]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 2306474,6-dichloro-2-ethyl-5-nitropyrimidine

Product 1

HCID 5220474,6-dichloro-2-ethylpyrimidin-5-amineYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

4,6-Dichloro-5-nitro-2-ethylpyrimidine (185 g, 0.83 mol) was dissolved in methanol (1.5 L) and reduced under 15 p.s.i. H2 in the presence of Raney nickel (30 g) for 5 hr. The mixture was filtered through Celite (washing well with MeOH) and the filtrate was evaporated to dryness to give 159.1 g (0.83 mol, quantitative yield) of the title compound as a chromatographically pure (silica gel plates, developed with EtOAc:hexanes, 3:1) dark liquid which was used directly in the next step.

Workup

  1. filtrationThe mixture was filtered through Celite (
  2. washwashing well with MeOH) and the filtrate
  3. customwas evaporated to dryness

Sources & evidence

ORD record
ord-2d015bf70a38492d953c1045a0440294
Source dataset
uspto-grants-1991_10
Patent number
US05057517

Reaction notes

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