Methyl 5-(acetoxymethyl)-7-chloro-s-triazolo[1,5-a]pyrimidine-2-carboxylate → HCID 178499051, compound

HRID 1755902Notes

Reaction equation

HRID 1755902 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[C:10](Cl)[N:9]2[N:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[N:15]=[C:8]2[N:7]=1)(=O)C.O.[SH2:21].[Na]>CO>[OH:4][CH2:5][C:6]1[CH:11]=[C:10]([SH:21])[N:9]2[N:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[N:15]=[C:8]2[N:7]=1

Participants

4

Reactant 2

HCID 19917996Methyl 5-(acetoxymethyl)-7-chloro-s-triazolo[1,5-a]pyrimidine-2-carboxylateHCID 53442613Sodium hydrogen sulfide hydrate

Product 1

HCID 178499051HCID 178499051, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 5-(acetoxymethyl)-7-chloro-s-triazolo[1,5-a]pyrimidine-2-carboxylate (380 mg) (1.33 mmol) are dissolved in 20 ml of methanol. After the addition of 296 mg (4 mmol) of sodium hydrogen sulphide monohydrate the mixture is stirred at 60° C. for 5 hours. The reaction mixture is concentrated and brought to pH 3 with dilute aqueous hydrochloric acid. The product is filtered off under suction, washed with water/methanol and crystallized from methanol. There are obtained 290 mg of methyl 5-(hydroxymethyl)-7-mercapto-s-triazolo[1,5-a]pyrimidine-2-carboxylate as a brown powder.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. filtrationThe product is filtered off under suction
  3. washwashed with water/methanol
  4. customcrystallized from methanol

Sources & evidence

ORD record
ord-d323a83161a3431cb5431896bd4748b5
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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