Ethyl orthoformate → 7-Chloro-5-methylthio-1,2,4-triazolo[4,3-c]pyrimidine

HRID 371384

Reaction equation

HRID 371384 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][NH2:9])[N:5]=[C:4]([S:10][CH3:11])[N:3]=1.[CH:12](OCC)(OCC)OCC>>[Cl:1][C:2]1[N:3]=[C:4]([S:10][CH3:11])[N:5]2[CH:12]=[N:9][N:8]=[C:6]2[CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 14845464-Chloro-6-hydrazinyl-2-(methylsulfanyl)pyrimidine

Product 1

HCID 135198587-Chloro-5-methylthio-1,2,4-triazolo[4,3-c]pyrimidine

Procedure

A mixture of 7.0 g (0.037 mole) of 4-chloro-6-hydrazino-2-methylthiopyrimidine and 100 ml of triethyl orthoformate was heated at reflux for 48 hours. Cooling provided a precipitate which was isolated by filtration, and then recrystallized from an ethanol-heptane mixture, with treatment with decolorizing charcoal. The product was red crystals of 7-chloro-5-methylthio-1,2,4-triazolo[4,3-c]pyrimidine, m.p. 164°-165° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 hours
  3. temperatureCooling
  4. customprovided a precipitate which
  5. customwas isolated by filtration
  6. customrecrystallized from an ethanol-heptane mixture, with treatment with decolorizing charcoal

Sources & evidence

ORD record
ord-2132604681b044c0af377e7cdc2929c9
Source dataset
uspto-grants-1985_07
Patent number
US04532242

Linked notes

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