Methanol → 5,6,7,8-Tetrahydro-7-(phenylmethyl)pyrido(3,4-d)pyrimidin-4(3H)-one
Reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][C:12](=O)[CH:11](C(OCC)=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[O-].[Na+].CO.[C:26]([OH:29])(=O)C.[CH:30]([NH2:32])=[NH:31]>>[CH2:2]([N:9]1[CH2:14][CH2:13][C:12]2[C:26](=[O:29])[NH:32][CH:30]=[N:31][C:11]=2[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1Participants
5
Procedure
1-Benzyl-3-ethoxycarbonyl-4-piperidone hydrochloride (12.89 g, 43.3 mmol) was suspended in a sodium methoxide solution in methanol (25% wt/wt, 50 mL, 216.2 mmol) and formamidine acetate (5.4 g, 51.9 mmol) was added to the mixture. The reaction mixture was refluxed until all of the starting material was consumed (2 h). The methanol was removed under vacuum, and the resulting white solid was dissolved in a 3:1 mixture of chloroform: isopropanol. The mixture was washed with water and brine, dried over Na2SO4, filtered and evaporated to give the desired product as a white solid (9.4 g, 90%).
Workup
- additionwas added to the mixture
- temperatureThe reaction mixture was refluxed until all of the starting material
- customwas consumed (2 h)
- customThe methanol was removed under vacuum
- dissolutionthe resulting white solid was dissolved in a 3:1 mixture of chloroform
- washThe mixture was washed with water and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-8c7038490be9444a9b4c0736461544f5
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07414131B2
Reaction notes
Loading…