Dimethyl Sulfate → 1-Methyl-2-isopropylamino-5-methoxycarbonylpyrimidinium hydroxide

HRID 374427Notes

Reaction equation

HRID 374427 reaction equation
[CH:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][N:6]=1)([CH3:3])[CH3:2].S(OC)(O[CH3:19])(=O)=O>O1CCCC1>[OH-:12].[CH3:19][N+:10]1[CH:9]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:7]=[N:6][C:5]=1[NH:4][CH:1]([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 19698832Methyl 2-(isopropylamino)pyrimidine-5-carboxylate

Product 1

HCID 196988161-Methyl-2-isopropylamino-5-methoxycarbonylpyrimidinium hydroxideYield 233.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 27.45 g (0.140 mol) of 2-isopropylamino-5-methoxycarbonylpyrimidine and 56 ml (2 eq; 0.59 mol) of dimethyl sulfate in 440 ml of anhydrous tetrahydrofuran is refluxed for 24 hours. The reaction medium is extracted with ethyl acetate and water. Purification on silica gel (eluent: 95 CH2Cl2 [sic]/5% MeOH/saturation with gaseous NH3) of the oil resulting from the evaporation of the aqueous phases gives 37.2 g of 1-methyl-2-isopropylamino-5-methoxycarbonylpyrimidinium hydroxide (yield: 82%).

Workup

  1. temperatureis refluxed for 24 hours
  2. extractionThe reaction medium is extracted with ethyl acetate and water
  3. customPurification on silica gel (eluent: 95 CH2Cl2 [sic]/5% MeOH/saturation with gaseous NH3) of the oil
  4. customresulting from the evaporation of the aqueous phases

Sources & evidence

ORD record
ord-6f62125b9280437c92a53b714c40207b
Source dataset
uspto-grants-1996_01
Patent number
US05480884

Reaction notes

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