Dimethyl Sulfate → 3-Methoxy-2-pyridone

HRID 2268147Notes

Reaction equation

HRID 2268147 reaction equation
[NH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]1=[O:7].[OH:8][C:9]1C(=O)N(CC2C=CC(OC)=CC=2)CCC=1C(=O)CC.COS(OC)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:9][O:8][C:3]1[C:2](=[O:7])[NH:1][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6497Dimethyl Sulfate2×HCID 88712-PyridoneHCID 10796Cesium carbonate2×HCID 12037815AGN-PC-0NHKTJ

Product 1

HCID 887313-Methoxy-2-pyridone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

said pyridinone compound of Formula (6.0.0) by methylation with dimethylsulfate; wherein a reaction mixture is established with dimethylformamide (DMF) solvent in the presence of cesium carbonate, Cs2CO3, with gradual addition of said dimethylsulfate over a period of 30 minutes, while said reaction mixture temperature is kept at from 20° to 25° C.; and thereafter, said reaction mixture is maintained at said temperature and stirred for 16 hours; whereby there is produced a 3-methoxy-pyridinone compound N-protected by p-methoxybenzyl, of Formula (7.0.0):

Workup

  1. customreaction mixture temperature
  2. customis kept at from 20° to 25° C.
  3. customreaction mixture
  4. temperatureis maintained

Sources & evidence

ORD record
ord-44454ab74c1a45a59974626b55a6ff8d
Source dataset
uspto-grants-2001_12
Patent number
US06326495B2

Reaction notes

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