p-Toluenesulfonic acid → HCID 178498584, compound

HRID 1032582Notes

Reaction equation

HRID 1032582 reaction equation
[OH:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][OH:12])[N:10]=[C:6]2[N:5]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[CH:3]=1.CN(C=O)C.[C:22](OC(=O)C)(=[O:24])[CH3:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:22]([O:12][CH2:11][C:9]1[N:10]=[C:6]2[N:5]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[CH:3]=[C:2]([OH:1])[N:7]2[N:8]=1)(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 178498586HCID 178498586, compound

Product 1

HCID 178498584HCID 178498584, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 25.7 g of 7-hydroxy-2-hydroxymethyl-5-methoxycarbonyl-s-triazolo[1,5-a]pyrimidine, 200 of DMF, 47 ml of acetic anhydride and 1 g of p-toluenesulfonic acid was stirred at 60° C. for 24 hours. The reaction mixture was condensed and 100 ml of methanol was added to the crystals precipitated residue, and the mixture was stirred. Then, crystals were collected by filtration, washed with methanol and dried to obtain 8.9 g of the title compound.

Workup

  1. additionwas added to the crystals
  2. customprecipitated residue
  3. stirringthe mixture was stirred
  4. filtrationThen, crystals were collected by filtration
  5. washwashed with methanol
  6. customdried

Sources & evidence

ORD record
ord-6ec77b0207f6434da0834788576b5971
Source dataset
uspto-grants-1990_09
Patent number
US04958019

Reaction notes

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