Cesium carbonate → HCID 131734720, compound

HRID 1774424Notes

Reaction equation

HRID 1774424 reaction equation
[Cl:1][C:2]1[N:7]([CH3:8])[C:6](=O)[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][CH:2]1[N:7]([CH3:8])[CH:6]=[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 131734720HCID 131734720, compoundYield 62.7%

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(31-1)-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-94712be06dd642c0a0acd078ec328195
Source dataset
uspto-grants-2016_02
Patent number
US09260413B2

Reaction notes

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