3-Methyl-6-(methylamino)-2-(methylthio)-4(3H)-pyrimidinone → 3-Methyl-6-(methylamino)-4(3H)-pyrimidinone

HRID 1660871Notes

Reaction equation

HRID 1660871 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([NH:9][CH3:10])[N:4]=[C:3]1SC>CO.[Ni].O>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([NH:9][CH3:10])[N:4]=[CH:3]1

Participants

5

Reactant 1

HCID 8169183-Methyl-6-(methylamino)-2-(methylthio)-4(3H)-pyrimidinone2×

Product 1

HCID 552881473-Methyl-6-(methylamino)-4(3H)-pyrimidinone

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Referring to scheme 1, 3-methyl-6-(methylamino)-2-(methylthio)pyrimidin-4(3H)-one (compound 1A; 650 mg, 0.35 mmol, 1 eq) was suspended in methanol (5 ml). A large excess of Raney Nickel slurried in water was added (approx 5 ml) and the mixture stirred at room temperature overnight to yield compound 1B. The product was confirmed by LC-MS. The mixture was filtered and the solid washed several times with methanol. The filtrate was then removed in vacuo and the residue was purified by flash chromatography with 1:10 MeOH:DCM to leave 3-methyl-6-(methylamino)pyrimidin-4(3H)-one (compound 1B) as a yellow/green solid (380 mg, 86%). 1H NMR (400 MHz, MeOD) δ ppm 2.78 (s, 3H) 3.35 (s, 3H) 5.22 (br. s., 1H) 8.10 (br. s., 1H); [M+H] calc'd for C5H7N3O, 126; found, 126.

Workup

  1. additionwas added (approx 5 ml)

Sources & evidence

ORD record
ord-d4abfb825f714faf92e908e3166c8987
Source dataset
uspto-grants-2011_10
Patent number
US08030317B2

Reaction notes

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