Dimethyl Sulfate → HCID 67453501, compound

HRID 876754Notes

Reaction equation

HRID 876754 reaction equation
[C:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][NH:11][C:12](=[O:22])[C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:25]OS(OC)(=O)=O>CN(C=O)C>[C:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][N:11]([CH3:25])[C:12](=[O:22])[C:13]=1[O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 136247265HCID 136247265, compound

Product 1

HCID 67453501HCID 67453501, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using a procedure described in U.S. Patent Publication No. 2005/0090668, a solution of 5-benzyloxy-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid tert-butyl ester was first treated with NaH (1.3 equiv.) in DMF followed by the addition of dimethylsulfate (1.3 equiv.) to give mainly the desired product after 2 h at room temperature. The reaction mixture was quenched with cold HCl (1N, 30 vol.) and extracted with EtOAc (3×30 vol.). The combined organic extracts were washed with dilute HCl and brine, dried and concentrated to an oil. Chromatography of the crude product (eluted with 40-60% EtOAc/hexane) gave 88% yield of the N-methylated compound (Synthon A).

Sources & evidence

ORD record
ord-6c81113524e34f3db07262b8d8154547
Source dataset
uspto-grants-2015_03
Patent number
US08987272B2

Reaction notes

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