HCID 178499517, compound → HCID 178499509, compound

HRID 1682536Notes

Reaction equation

HRID 1682536 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:13])[N:5]=[C:4](S)[N:3]=1>CO.[Ni]>[CH3:12][O:11][C:9](=[O:10])[CH2:8][C:7]1[C:2]([OH:1])=[N:3][CH:4]=[N:5][C:6]=1[CH3:13]

Participants

4

Reactant 1

HCID 178499517HCID 178499517, compound

Product 1

HCID 178499509HCID 178499509, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of methyl (4-hydroxy-2-mercapto-6-methyl-5-pyrimidinyl)-acetate (160 g, 0.75 mol) and Raney-Nickel in water (1.51) is refluxed for 16 hours. The reaction mixture is filtered and the filtrate concentrated under reduced pressure to 1/10 of the original volume. Filtration of the precipitate and drying gives methyl(4-hydroxy-6-methyl-5-pyrimidinyl)-acetate in form of colorless crystals (116 g, 85%). 1H-NMR (DMSO):12.4 (s, 1H); 8.0 (s, 1H); 3.6 (s, 3H); 3.4 (s, 2H); 2.1 (s, 3H)

Workup

  1. temperatureis refluxed for 16 hours
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate concentrated under reduced pressure to 1/10 of the original volume
  4. filtrationFiltration of the precipitate
  5. customdrying

Sources & evidence

ORD record
ord-0084994d84774eea8ea4721d0d9facc4
Source dataset
uspto-grants-1997_06
Patent number
US05635508

Reaction notes

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