Methyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylate → Methyl 4-methoxypyrimidine-5-carboxylate

HRID 2264162Notes

Reaction equation

HRID 2264162 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][N:6]=[C:5](SC)[N:4]=1.[H][H]>[Ni].CO>[CH3:1][O:2][C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][N:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 12828997Methyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 12828992Methyl 4-methoxypyrimidine-5-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2.2 g of methyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylate, 15 g of Raney nickel (washed with methanol to remove water) and 200 mL of methanol was stirred under 1 atm hydrogen overnight. Conversion was incomplete by LCMS so the mixture was filtered and treated with 15 g of fresh Raney nickel under hydrogen overnight. After filtration and concentration under reduced pressure, purification by flash chromatography (0%-10% ethyl acetate in hexanes) gave the product as white crystalline solid: MS (m+1)=169.1; 1H NMR (400 MHz, CDCl3) 9.0 (s, 1H), 8.82 (s, 1H), 4.1 (s, 3H), 3.9 (s, 3H).

Workup

  1. filtrationwas filtered
  2. additiontreated with 15 g of fresh Raney nickel under hydrogen overnight
  3. filtrationAfter filtration and concentration
  4. customunder reduced pressure, purification by flash chromatography (0%-10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7f4a2c62b43e43edba2533c7006ab1ca
Source dataset
uspto-grants-2010_12
Patent number
US07855201B2

Reaction notes

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