Cesium carbonate → HCID 67406083, compound

HRID 869293Notes

Reaction equation

HRID 869293 reaction equation
[Cl:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([OH:10])=[CH:4][N:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([O:10][CH2:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 67405891HCID 67405891, compound

Product 1

HCID 67406083HCID 67406083, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 9.60 g (59.8 mmol) 2-chloro-5-hydroxy-3-methylpyrimidin-4(3H)-one in 300 ml DMF was added 20.4 ml (149 mmol) PMBCl, and 48.7 g (149 mmol) Cs2CO3. The reaction mixture was heated to 60° C. for 3 h, cooled to rt, quenched with 200 ml water, extracted with 500 ml EtOAc, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography (330 g silica gel, 3-80% EtOAc:hexane) gave 10 g (60% yield) of 2-chloro-5-[(4-methoxybenzyl)oxy]-3-methylpyrimidin-4(3H)-one. LCMS [M+H]+=281.0.

Workup

  1. temperaturecooled to rt
  2. customquenched with 200 ml water
  3. extractionextracted with 500 ml EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (330 g silica gel, 3-80% EtOAc:hexane)

Sources & evidence

ORD record
ord-a0696ab9afb44a798d811192c76f7419
Source dataset
uspto-grants-2015_03
Patent number
US08969364B2

Reaction notes

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