Methyl Lactate → HCID 18619176, compound

HRID 1862256Notes

Reaction equation

HRID 1862256 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[C:12](Cl)=[N:13][C:14]([CH3:17])=[N:15][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:19]([O:24][CH3:25])(=[O:23])[CH:20]([CH3:22])[OH:21]>O1CCCC1>[CH2:3]([O:10][C:11]1[C:12]([O:21][CH:20]([C:19]([O:24][CH3:25])=[O:23])[CH3:22])=[N:13][C:14]([CH3:17])=[N:15][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11040Methyl LactateHCID 24758Sodium hydrideHCID 14642739HCID 14642739, compound

Product 1

HCID 18619176HCID 18619176, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride is added to a mixture of 5-benzyloxy-4-chloro-2-methylpyrimidine, methyl lactate and tetrahydrofuran at 0° C. The mixture is stirred at room temperature for 1 hour, then, stirred at 90° C. for 30 minutes. The reaction solution was cooled to room temperature and poured into ice water, and extracted with ethyl acetate. The organic layer is washed with dilute hydrochloric acid and saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue is subjected to silica gel column chromatography to obtain 5-benzyloxy-4-{1-(methoxycarbonyl)ethoxy}-2-methylpyrimidine

Workup

  1. stirringstirred at 90° C. for 30 minutes
  2. temperatureThe reaction solution was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with dilute hydrochloric acid and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bb049718c08840eebe5d927a08bedb7c
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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