Methyl iodide → 3-Methyl-2-(methylthio)-4(3H)-pyrimidinone

HRID 709972

Reaction equation

HRID 709972 reaction equation
[CH3:1][S:2][C:3]1[NH:8][C:7](=[O:9])[CH:6]=[CH:5][N:4]=1.[Li+].[CH3:11][Si]([N-][Si](C)(C)C)(C)C.CI>CN(C=O)C>[CH3:11][N:8]1[C:7](=[O:9])[CH:6]=[CH:5][N:4]=[C:3]1[S:2][CH3:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 798232-(Methylthio)-1H-pyrimidin-4-oneHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 1387273-Methyl-2-(methylthio)-4(3H)-pyrimidinoneYield 62.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 0° C. suspension of 2-(methylthio)pyrimidin-4(3H)-one (2.0 g, 14.1 mmol) in DMF (40 mL) was treated with solid LiHMDS (3.06 g, 18.3 mmol), followed by methyl iodide (1.14 mL, 18.3 mmol), warmed to RT and stirred overnight. The mixture was quenched with water, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 3-methyl-2-(methylthio)pyrimidin-4(3H)-one (1.37 g, 62%). 1H NMR (400 MHz, DMSO-d6): δ 7.83 (d, J=6.5 Hz, 1H), 6.17 (d, J=6.5 Hz, 1H), 3.39 (s, 3H), 2.54 (s, 3H); MS (ESI) m/z: 157.1 (M+H+).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc (3×)
  3. dry with materialthe combined organics were dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. custompurified via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-ba872198cc934377b4d46c19bd45c718
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Linked notes

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