Methanol → Methyl 2-(4-methyl-6-oxo-2-phenyl-1,6-dihydropyrimidin-5-yl)pentanoate
Reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:5][C:6](=[O:15])[C:7]=1[CH:8]([CH2:12][CH2:13][CH3:14])[C:9]([OH:11])=[O:10].S(Cl)(Cl)=O.[CH3:26]O>>[CH3:1][C:2]1[N:3]=[C:4]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:5][C:6](=[O:15])[C:7]=1[CH:8]([CH2:12][CH2:13][CH3:14])[C:9]([O:11][CH3:26])=[O:10]Participants
Procedure
The 2-(4-methyl-6-oxo-2-phenyl-1,6-dihydropyrimidin-5-yl)pentanoic acid (17.16 g) was suspended in dry methanol (150 mL) and thionyl chloride (87 mL; 120 mmol) was added dropwise. The stirred reaction mixture was heated at reflux for 18 h. After cooling, the white precipitate was filtered off, washed with methanol and the filtrate was concentrated under reduced pressure. The residue was suspended in ethyl acetate (25 mL) and heptane (50 mL) was added. The white precipitate was filtered and dried under reduced pressure. The filtrate was concentrated and the residue was precipitate another time with the same procedure to furnish 12.1 g (80% overall yield) of the title compound as a white powder. ESI/APCI(+): 301 (M+H); ESI/APCI(−): 299 (M−H).
Workup
- customThe stirred reaction mixture
- temperaturewas heated
- temperatureat reflux for 18 h
- temperatureAfter cooling
- filtrationthe white precipitate was filtered off
- washwashed with methanol
- concentrationthe filtrate was concentrated under reduced pressure
- additionheptane (50 mL) was added
- filtrationThe white precipitate was filtered
- customdried under reduced pressure
- concentrationThe filtrate was concentrated
- customthe residue was precipitate another time with the same procedure
- customto furnish
Sources & evidence
- ORD record
- ord-bacee78d328d4f53bf92cd9b6c4f61d6
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906906B2
Reaction notes
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