2-Acetoxymethyl7-chloro-5-methoxycarbonyl-s-triazolo[1,5-a]pyrimidine → HCID 178498635, compound

HRID 1755913Notes

Reaction equation

HRID 1755913 reaction equation
[C:1]([O:4][CH2:5][C:6]1[N:19]=[C:9]2[N:10]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[C:13](Cl)[N:8]2[N:7]=1)(=[O:3])[CH3:2].O.[SH2:21].[Na]>CO>[C:1]([O:4][CH2:5][C:6]1[N:19]=[C:9]2[N:10]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[C:13]([SH:21])[N:8]2[N:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 156727662-Acetoxymethyl7-chloro-5-methoxycarbonyl-s-triazolo[1,5-a]pyrimidineHCID 53442613Sodium hydrogen sulfide hydrate

Product 1

HCID 178498635HCID 178498635, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 2-(acetoxymethyl)-7-chloro-s-triazolo[1,5-a]pyrimidine-5-carboxylate (370 mg) (1.3 mmol) are dissolved in 10 ml of methanol. After the addition of 289 mg (3.9 mmol) of sodium hydrogen sulphide hydrate the mixture is stirred at 60° C. for 4 hours. The yellow solution is concentrated in a vacuum. The residue is dissolved in water and the product is precipitated at pH 3 with 3N aqueous hydrochloric acid. The precipitate is filtered off under suction and crystallized from methanol. There are obtained 360 mg of methyl 2-(acetoxymethyl)-7-mercapto-s-triazolo[1,5-a]pyrimidine-5-carboxylate.

Workup

  1. concentrationThe yellow solution is concentrated in a vacuum
  2. dissolutionThe residue is dissolved in water
  3. customthe product is precipitated at pH 3 with 3N aqueous hydrochloric acid
  4. filtrationThe precipitate is filtered off under suction
  5. customcrystallized from methanol

Sources & evidence

ORD record
ord-acea53ddaf2c42c282e9444685db86f8
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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