Methanol → Methyl 2-(4,6-dioxo-2-(piperidin-1-yl)-1,4,5,6-tetrahydropyrimidin-5-yl)pentanoate

HRID 1399763Notes

Reaction equation

HRID 1399763 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[C:11]([CH:12]([CH2:16][CH2:17][CH3:18])[C:13]([OH:15])=[O:14])=[C:10]([OH:19])[N:9]=[C:8]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[N:7]=1.[CH3:26]O>>[O:5]=[C:6]1[CH:11]([CH:12]([CH2:16][CH2:17][CH3:18])[C:13]([O:15][CH3:26])=[O:14])[C:10](=[O:19])[NH:9][C:8]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[N:7]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178447459HCID 178447459, compound

Product 1

HCID 66955652Methyl 2-(4,6-dioxo-2-(piperidin-1-yl)-1,4,5,6-tetrahydropyrimidin-5-yl)pentanoate

Procedure

To a solution cold solution of methanol (50 mL) was added thionyl chloride (7.25 mL; 100 mmol) dropwise. The acidic solution was added to a flask containing 2-(4,6-dihydroxy-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoic acid (3.07 g; 10.4 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-52a7b312ae83449a87cb87b3a072ba1b
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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