Methyl Lactate → 5-Benzyloxy-4-{1-(methoxycarbonyl)ethoxy}pyrimidine

HRID 1862270Notes

Reaction equation

HRID 1862270 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[C:12](Cl)=[N:13][CH:14]=[N:15][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:18]([O:23][CH3:24])(=[O:22])[CH:19]([CH3:21])[OH:20]>O1CCCC1>[CH2:3]([O:10][C:11]1[C:12]([O:20][CH:19]([C:18]([O:23][CH3:24])=[O:22])[CH3:21])=[N:13][CH:14]=[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 136077245-(Benzyloxy)-4-chloropyrimidine

Product 1

HCID 186192295-Benzyloxy-4-{1-(methoxycarbonyl)ethoxy}pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride is added to a mixture of 5-benzyloxy-4-chloropyrimidine, methyl lactate and tetrahydrofuran at 0° C. The mixture is stirred at room temperature for 1 hour, then, stirred for 30 minutes at 90° C. The reaction solution is cooled to room temperature, then, 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}pyrimidine.

Workup

  1. stirringstirred for 30 minutes at 90° C
  2. temperatureThe reaction solution is 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-44c2343bffa247c1bd8b29b9190ebe5b
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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