Methyl iodide → 2-methylthio-5-(2-hydroxyethyl)-3,6-dimethyl-3H-pyrimidin-4-one

HRID 2222279Notes

Reaction equation

HRID 2222279 reaction equation
[CH3:1][S:2][C:3]1[NH:8][C:7](=[O:9])[C:6]([CH2:10][CH2:11][OH:12])=[C:5]([CH3:13])[N:4]=1.[H-].[Na+].[CH3:16]I>CN(C=O)C>[CH3:1][S:2][C:3]1[N:8]([CH3:16])[C:7](=[O:9])[C:6]([CH2:10][CH2:11][OH:12])=[C:5]([CH3:13])[N:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1354111545-(2-hydroxyethyl)-6-methyl-2-(methylsulfanyl)-4(3H)-pyrimidinone

Product 1

HCID 693142522-methylthio-5-(2-hydroxyethyl)-3,6-dimethyl-3H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 2-methylthio-5-(2-hydroxyethyl)-6-methyl-3H-pyrimidin-4-one (34 g, 0.17 mol) in DMF (300 ml) was added slowly one equivalent of sodium hydride (55%, 7.4 g). Next was added slowly one equivalent of methyl iodide (10.5 ml). The mixture was stirred for two hours at 50° C., after which most of the DMF was removed in vaccuum. Water was added and the mixture was extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate and then concentrated and purified by flash chromatografy (eluens: ether followed by ether/methanol=9/1). Yield 20.3 g (56%), mp. 117-118° C.

Workup

  1. customafter which most of the DMF was removed in vaccuum
  2. additionWater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by flash chromatografy (eluens: ether followed by ether/methanol=9/1)

Sources & evidence

ORD record
ord-d35b47aa00154a578d283e4c3cb4713a
Source dataset
uspto-grants-2008_05
Patent number
US07371769B2

Reaction notes

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