Methanol → Methyl 2-(4-ethyl-6-oxo-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoate

HRID 1399737Notes

Reaction equation

HRID 1399737 reaction equation
S(Cl)(Cl)=O.[CH2:5]([C:7]1[N:8]=[C:9]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[NH:10][C:11](=[O:20])[C:12]=1[CH:13]([CH2:17][CH2:18][CH3:19])[C:14]([OH:16])=[O:15])[CH3:6].[CH3:27]O>>[CH2:5]([C:7]1[N:8]=[C:9]([N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[NH:10][C:11](=[O:20])[C:12]=1[CH:13]([CH2:17][CH2:18][CH3:19])[C:14]([O:16][CH3:27])=[O:15])[CH3:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 1363461602-(4-Ethyl-6-oxo-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoic acid

Product 1

HCID 136346171Methyl 2-(4-ethyl-6-oxo-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoate

Procedure

To a solution cold solution of methanol (40 mL) was added thionyl chloride (5.8 mL; 80 mmol) dropwise. The acidic solution was added to a flask containing 2-(4-ethyl-6-oxo-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoic acid (2.416 g; 7.86 mmol) and the mixture was heated to reflux for 18 h. The reaction mixture was concentrated under reduced pressure and the product was used as such in the next reaction.

Workup

  1. additionThe acidic solution was added to a flask
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 18 h
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customsuch in the next reaction

Sources & evidence

ORD record
ord-2d866ed5f9a7445cb3e666243bd7fc92
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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