Methyl atropate → 6-Phenyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-7-on

HRID 215692

Reaction equation

HRID 215692 reaction equation
C[O:2][C:3](=O)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH2:5].[NH2:13][C:14]1[N:18]=[CH:17][NH:16][N:15]=1>C(O)CCC>[C:6]1([CH:4]2[CH2:5][N:18]3[CH:17]=[N:16][N:15]=[C:14]3[NH:13][C:3]2=[O:2])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 193334Methyl atropateHCID 178418311HCID 178418311, compound

Product 1

HCID 1363441626-Phenyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-7-onYield 19%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 9.01 g (55.6 mmol) 2-phenyl acrylic acid methyl ester and 4.24 g (50.4 mmol) 3-amino-1,2,4-triazole in 41 ml n-butanol was refluxed for 24 hours. The solvent was removed under reduced pressure. The residue was treated with a small amount of ethanol and diethyl ether and cyclohexane were added. The diethyl ether is slowly removed under reduced pressure. The crude 6-phenyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-7-on precipitated during evaporation, was isolated by filtration and washed with diethyl ether. 6-phenyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-7-on was recrystallized from a small amount of ethanol. 2.04 g (19%) 6-phenyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-7-on was isolated (m.p. 184-186° C.).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was treated with a small amount of ethanol and diethyl ether and cyclohexane
  3. additionwere added
  4. customThe diethyl ether is slowly removed under reduced pressure
  5. customThe crude 6-phenyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-7-on precipitated during evaporation
  6. customwas isolated by filtration
  7. washwashed with diethyl ether
  8. custom6-phenyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-7-on was recrystallized from a small amount of ethanol

Sources & evidence

ORD record
ord-c3bbc2a121cf4b6aa6d4c1b9b88221d7
Source dataset
uspto-grants-2012_06
Patent number
US08192918B2

Linked notes

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