Dimethyl Sulfate → HCID 19698828, compound

HRID 374432Notes

Reaction equation

HRID 374432 reaction equation
[CH2:1]([NH:12][C:13]1[N:18]=[CH:17][C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:15][N:14]=1)[C:2]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=1.S(OC)(O[CH3:27])(=O)=O>C1COCC1>[OH-:5].[CH3:27][N+:18]1[CH:17]=[C:16]([C:19]([O:21][CH3:22])=[O:20])[CH:15]=[N:14][C:13]=1[NH:12][CH2:1][C:2]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 19698819HCID 19698819, compound

Product 1

HCID 19698828HCID 19698828, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.62 g .(8.6 mmol) of 2-veratrylamino-5-methoxycarbonylpyrimidine and 3.28 ml (4 eq) of dimethyl sulfate in 60 ml of anhydrous THF is refluxed for forty-eight hours. The mixture is extracted with ethyl acetate and water. Purification on silica gel (eluent: 3% MeOH/CH2Cl2 /NH3 in aqueous solution at 33%, 5.5 ml/100) of the oil resulting from evaporation of the aqueous phases gives 2.2 g of salt (yield: 76%).

Workup

  1. additionA mixture of 2.62 g
  2. extractionThe mixture is extracted with ethyl acetate and water
  3. customPurification on silica gel (eluent: 3% MeOH/CH2Cl2 /NH3 in aqueous solution at 33%, 5.5 ml/100) of the oil
  4. customresulting from evaporation of the aqueous phases

Sources & evidence

ORD record
ord-9fa71272c79940faa8cc5202ac9eefa1
Source dataset
uspto-grants-1996_01
Patent number
US05480884

Reaction notes

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