2-Chloro-6-propylthio-4-pyrimidinecarboxylic acid, (1,1-dimethylethyl) ester → tert-Butyl 2-chloropyrimidine-4-carboxylate

HRID 1872014Notes

Reaction equation

HRID 1872014 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:5]=[C:4](SCCC)[N:3]=1>C(O)C.[Ni]>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 572981932-Chloro-6-propylthio-4-pyrimidinecarboxylic acid, (1,1-dimethylethyl) ester

Product 1

HCID 57063961tert-Butyl 2-chloropyrimidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst3×HCID 702EthanolSolvent2×

Procedure

To a suspension of Raney® nickel (50% slurry in water, 10 g) in ethanol (20 ml) was added a solution of the product from step (ii) (3.83 g) in ethanol (20 ml). The mixture was stirred for 2 hours and treated with a further 5 g Raney® nickel. The mixture was stirred overnight and treated with a further 20 g Raney® nickel. After 1 hour the reaction mixture was filtered through Kieselguhr and the filtrate evaporated. The residue was purified by chromatography eluting with 5-10% ethyl acetate in isohexane. Yield 1.3 g.

Workup

  1. stirringThe mixture was stirred overnight
  2. filtrationAfter 1 hour the reaction mixture was filtered through Kieselguhr
  3. customthe filtrate evaporated
  4. customThe residue was purified by chromatography
  5. washeluting with 5-10% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-2a416997bebb454f853dab160062e672
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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