Water → Methyl 2-amino-6-[(p-tolylsulfonyl)oxy]-4-pyrimidinecarbamate

HRID 464772Notes

Reaction equation

HRID 464772 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:12][C:13]1[NH:14][C:15](=[O:24])[CH:16]=[C:17]([NH:19][C:20]([O:22][CH3:23])=[O:21])[N:18]=1.[OH-].[Na+].O>CC(C)=O>[NH2:12][C:13]1[N:18]=[C:17]([NH:19][C:20]([O:22][CH3:23])=[O:21])[CH:16]=[C:15]([O:24][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 135964809HCID 135964809, compound

Product 1

HCID 12857764Methyl 2-amino-6-[(p-tolylsulfonyl)oxy]-4-pyrimidinecarbamate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

2.08 g (11 mmol) of p-toluenesulfonyl chloride in 20 ml of acetone are added dropwise to a solution of 1.47 g (8 mmol) of methyl 2-amino-1,6-dihydro-6-oxo-4-pyrimidinecarbamate, 12 ml of 1N sodium hydroxide, 5 ml of water and 50 ml of acetone. The mixture is stirred at room temperature for 18 hours. After filtration of the precipitate, the solvent is evaporated under reduced pressure. The residue is dissolved in a mixture of ethyl acetate and water, the organic phase is separated, dried and evaporated under reduced pressure. Crystallization from methylene chloride/methanol yields pure methyl 2-amino-6-[(p-toluenesulfonyl)oxy]-4-pyrimidinecarbamate of meltig point 188°-189°.

Workup

  1. filtrationAfter filtration of the precipitate
  2. customthe solvent is evaporated under reduced pressure
  3. dissolutionThe residue is dissolved in a mixture of ethyl acetate and water
  4. customthe organic phase is separated
  5. customdried
  6. customevaporated under reduced pressure
  7. customCrystallization from methylene chloride/methanol

Sources & evidence

ORD record
ord-6589c271f5b644d19603600dbde2f5a7
Source dataset
uspto-grants-1985_10
Patent number
US04549019

Reaction notes

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