Acetic Acid → Ethyl 2-(benzylsulfanyl)-7-methyl[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate

HRID 619933Notes

Reaction equation

HRID 619933 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:4][N:3]=1.C(OC=[CH:19][C:20](=O)[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])C.[C:28](O)(=O)C>>[CH2:8]([S:7][C:5]1[N:6]=[C:2]2[N:1]=[CH:28][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:20]([CH3:19])[N:3]2[N:4]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 54463595Ethyl ethoxymethyleneacetoacetateHCID 178509291HCID 178509291, compound

Product 1

HCID 14155094Ethyl 2-(benzylsulfanyl)-7-methyl[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylateYield 33%

Procedure

A solution of 15 g (73 mmol) of 3-amino-5-benzylthio-1,2,4-triazole and 15.0 g (80.0 mmol) of ethyl ethoxymethyleneacetoacetate in 250 ml of glacial acetic acid was heated at reflux for 60 hours. After cooling the volume of the reaction was reduced to approximately one quarter of the original volume by evaporation at reduced pressure. The resulting residue was poured into water, and the solid which separated was collected by filtration, washed with water and dried to yield 7.88 g (33%) of the desired product as a solid, m.p. 98°-99° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. temperatureat reflux for 60 hours
  2. temperatureAfter cooling the volume of the reaction
  3. customwas reduced to approximately one quarter of the original volume by evaporation at reduced pressure
  4. additionThe resulting residue was poured into water
  5. customthe solid which separated
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-7559183b02f441e486fc99470bc638b2
Source dataset
uspto-grants-1989_04
Patent number
US04818273

Reaction notes

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