Methyl 7-chloro-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-5-carboxylate → HCID 178498634, compound

HRID 1755907Notes

Reaction equation

HRID 1755907 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[N:10]=[C:6]2[N:5]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:3]=1.O.[SH2:17].[Na]>CO>[SH:17][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[N:10]=[C:6]2[N:5]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:3]=1

Participants

4

Reactant 2

HCID 14852618Methyl 7-chloro-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-5-carboxylateHCID 53442613Sodium hydrogen sulfide hydrate

Product 1

HCID 178498634HCID 178498634, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 7-chloro-2-methyl-s-triazolo[1,5-a]pyrimidine-5-carboxylate (0.80 g) (3.53 mmol) are suspended in 35 ml of methanol and treated with 0.78 g (10.6 mmol) of sodium hydrogen sulphide hydrate. After stirring at 60° C. for 5 hours the mixture is concentrated and the residue is dissolved in 20 ml of water. The solution is acidified to pH 3 with 3N aqueous hydrochloric acid. The precipitated product is filtered off under suction and washed with water and methanol. After recrystallization from methanol/dichloromethane there is obtained 0.66 g of methyl 7-mercapto-2-methyl-s-triazolo[1,5-a]pyrimidine-5-carboxylate as yellow crystals of melting point 237° C. (dec.).

Workup

  1. concentrationis concentrated
  2. dissolutionthe residue is dissolved in 20 ml of water
  3. filtrationThe precipitated product is filtered off under suction
  4. washwashed with water and methanol
  5. customAfter recrystallization from methanol/dichloromethane there

Sources & evidence

ORD record
ord-09567eebbc3546739268131d09b09d0d
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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