p-Toluenesulfonic acid → HCID 178475878, compound

HRID 1032215Notes

Reaction equation

HRID 1032215 reaction equation
[OH:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[N:10]=[C:6]2[N:5]=[C:4]([CH2:12][OH:13])[CH:3]=1.CN([CH:17]=[O:18])C.[C:19]1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[C:17]([O:13][CH2:12][C:4]1[CH:3]=[C:2]([OH:1])[N:7]2[N:8]=[C:9]([CH3:11])[N:10]=[C:6]2[N:5]=1)(=[O:18])[CH3:19]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6228DimethylformamideHCID 178432391HCID 178432391, compound

Product 1

HCID 178475878HCID 178475878, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 33.06 g of 7-hydroxy-5-hydroxymethyl-2-methyl-s-triazolo[1,5-a]pyrimidine, 500 ml of DMF, 86 ml of anhydrous acetic acid and 1.5 g of p-toluenesulfonic acid was stirred in a bath at 50° C. for 6 hours. To an oily residue obtained by removing DMF was added 300 ml of isopropanol to dissolve therein, and the solution was added dropwise in 4 liters of ether. Precipitates were collected by filtration and dried to obtain 38.08 g of the title compound.

Workup

  1. customTo an oily residue obtained
  2. customby removing DMF
  3. additionwas added 300 ml of isopropanol
  4. dissolutionto dissolve
  5. additionthe solution was added dropwise in 4 liters of ether
  6. customPrecipitates
  7. filtrationwere collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-b039a17eac3f44ccbb650639da11126c
Source dataset
uspto-grants-1990_09
Patent number
US04956462

Reaction notes

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