Water → HCID 66519725, compound

HRID 869285Notes

Reaction equation

HRID 869285 reaction equation
CI.[Cl:3][C:4]1[NH:9][C:8](=[O:10])[C:7]([O:11][CH3:12])=[CH:6][N:5]=1.[C:13]([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[Cl:3][C:4]1[N:9]([CH3:13])[C:8](=[O:10])[C:7]([O:11][CH3:12])=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 11298128HCID 11298128, compound

Product 1

HCID 66519725HCID 66519725, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

128 g (0.9 mol) of MeI was added dropwise to the suspension of 2-chloro-5-methoxypyrimidin-4(3H)-one (74 g, crude, about 0.3 mol) and Cs2CO3 (195 g, 0.6 mol) in 600 mL of DMF at 0° C. and the reaction mixture was stirred at this temperature for 1 h, then warmed to r.t., and stirred another 1 h. The mixture was poured into water and extracted with EtOAc several times. The extract was washed with water, brine and dried over Na2SO4 before being filtered and concentrated to give a crude product, which was purified by silica gel chromatography to give 31.2 g (71.2%) of 2-chloro-5-methoxy-3-methylpyrimidin-4(3H)-one. 1H-NMR (CDCl3, 400 MHz) δ 7.37 (s, 1H), 3.80 (s, 3H), 3.61 (s, 3H). MS (ESI) m/z (M+H)+ 175.0/176.0.

Workup

  1. stirringstirred another 1 h
  2. extractionextracted with EtOAc several times
  3. washThe extract was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationbefore being filtered
  6. concentrationconcentrated
  7. customto give a crude product, which
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-4407b17f1e294a229961f39c156cac73
Source dataset
uspto-grants-2015_03
Patent number
US08969364B2

Reaction notes

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