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

HRID 464783Notes

Reaction equation

HRID 464783 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:13])[CH:5]=[C:6]([NH:8][C:9]([O:11][CH3:12])=[O:10])[N:7]=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>CN1CCOCC1.C(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[C:4]([O:13][S:20]([C:17]2[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=2)(=[O:22])=[O:21])[N:3]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 135964809HCID 135964809, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 79724-MethylmorpholineSolvent

Procedure

A stirred suspension of 500 g of methyl 2-amino-1,6-dihydro-6-oxo-4-pyrimidinecarbamate in 1.45 l of N-methylmorpholine and 9 l of methylene chloride is heated to reflux temperature. Subsequently, 815 g of toluene-4-sulfonyl chloride are added thereto and the mixture is stirred at reflux for 16 hours. The mixture is evaporated at 40° in a water-jet vacuum and the residue is treated with 9 l of water. The insoluble material is filtered off under suction and washed firstly with 5 l of water and thereafter with 5 l of ether. After drying at 40° in vacuo, there is obtained light brown methyl 2-amino-6-[(p-tolylsulfonyl)oxy]-4-pyrimidinecarbamate of melting point 188°-190°. A sample recrystallized from acetonitrile has a melting point of 190°-192°.

Workup

  1. temperatureis heated
  2. temperatureto reflux temperature
  3. temperatureat reflux for 16 hours
  4. customThe mixture is evaporated at 40° in a water-jet vacuum
  5. additionthe residue is treated with 9 l of water
  6. filtrationThe insoluble material is filtered off under suction
  7. washwashed firstly with 5 l of water
  8. customAfter drying at 40° in vacuo

Sources & evidence

ORD record
ord-efa6afa8eb6c41078df797b10c8440e8
Source dataset
uspto-grants-1985_10
Patent number
US04549019

Reaction notes

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