Methanol → Methyl 2-(6-oxo-4-phenyl-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoate
Reaction equation
S(Cl)(Cl)=O.[O:5]=[C:6]1[NH:11][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:9][C:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:7]1[CH:24]([CH2:28][CH2:29][CH3:30])[C:25]([OH:27])=[O:26].[CH3:31]O>>[O:5]=[C:6]1[NH:11][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:9][C:8]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:7]1[CH:24]([CH2:28][CH2:29][CH3:30])[C:25]([O:27][CH3:31])=[O:26]Participants
4
Procedure
To a solution cold solution of methanol (20 mL) was added thionyl chloride (2.90 mL; 40 mmol) dropwise. The acidic solution was added to a flask containing 2-(6-oxo-4-phenyl-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoic acid (1.67 g; 4.71 mmol) and the mixture was heated to reflux for 18 h. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in water and neutralized with a saturated solution of sodium hydrogen carbonate. The suspension was extracted twice with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The product was used as such in the next reaction.
Workup
- additionThe acidic solution was added to a flask
- temperaturethe mixture was heated
- temperatureto reflux for 18 h
- concentrationThe reaction mixture was concentrated under reduced pressure
- dissolutionthe residue was dissolved in water
- extractionThe suspension was extracted twice with ethyl acetate
- washthe combined organic layers were washed with brine
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customsuch in the next reaction
Sources & evidence
- ORD record
- ord-d576a46462ba4d6288823c8938d4e4a5
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906906B2
Reaction notes
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