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

HRID 1755882Notes

Reaction equation

HRID 1755882 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 separated 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 separated product is filtered off under suction
  4. washwashed with water and methanol
  5. customAfter recrystallization from methanol/dichloromethane there

Sources & evidence

ORD record
ord-b36d5428d7ec4ddba2d7a016e7914e75
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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