Dimethyl malonate → 2-benzylsulfanyl-7-hydroxy-1H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one

HRID 844967Notes

Reaction equation

HRID 844967 reaction equation
C[O-].[Na+].[C:4]([O:11]C)(=O)[CH2:5][C:6](OC)=[O:7].[NH2:13][C:14]1[N:18]=[C:17]([S:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:16][N:15]=1>CO.C(O)C>[CH2:20]([S:19][C:17]1[N:18]=[C:14]2[N:13]=[C:4]([OH:11])[CH:5]=[C:6]([OH:7])[N:15]2[N:16]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 7943Dimethyl malonateHCID 10942334Sodium MethoxideHCID 178509291HCID 178509291, compound

Product 1

HCID 1785166162-benzylsulfanyl-7-hydroxy-1H-[1,2,4]triazolo[1,5-a]pyrimidin-5-oneYield 127.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 125 g (0.58 mol) of a 25% solution of sodium methoxide in methanol dissolved in 100 ml of absolute ethanol was treated with 66.3 ml (0.29 mol) of dimethyl malonate followed by 60.0 g (0.20 mol) of 3-amino-5-benzylthio-1,2,4-triazole. The resulting solution was heated at reflux for 5 days. On cooling to room temperature the solid which had separated was collected by filtration, washed with cold ethanol and dissolved in 1000 ml of water. The resulting yellow solution was acidified with concentrated HCl to precipitate a solid. The solid was collected by filtration and dried to yield 70.1 g (82%) of the desired product as a white solid, m.p. 199°-210° C. (decompostion). IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 5 days
  3. customhad separated
  4. filtrationwas collected by filtration
  5. washwashed with cold ethanol
  6. dissolutiondissolved in 1000 ml of water
  7. customto precipitate a solid
  8. filtrationThe solid was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-c45cd294a9004f46b2d03081cd50f1cf
Source dataset
uspto-grants-1988_07
Patent number
US04755212

Reaction notes

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