Methanol → HCID 19781550, compound

HRID 1885881Notes

Reaction equation

HRID 1885881 reaction equation
[H-].[Na+].[N:3]1([C:9]2[N:14]=[C:13]([CH2:15]Cl)[C:12]([C:17]([O:19][CH3:20])=[O:18])=[CH:11][N:10]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:21][OH:22]>>[N:3]1([C:9]2[N:14]=[C:13]([CH2:15][O:22][CH3:21])[C:12]([C:17]([O:19][CH3:20])=[O:18])=[CH:11][N:10]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 19781548HCID 19781548, compound

Product 1

HCID 19781550HCID 19781550, compoundYield 44%

Procedure

Sodium hydride (0.19 g; 7.8 mmoles) was added to 50 ml of methanol, and 2.1 g (7.8 mmoles) of 2-piperidino-4-chloromethyl-5-methoxycarbonylpyrimidine was added at room temperature. The mixture was stirred for 3 hours. After the solvent was evaporated, water was added to the residue and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 0.90 g (yield 44%) of the desired product as a white solid.

Workup

  1. additionwas added at room temperature
  2. customAfter the solvent was evaporated
  3. additionwater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-737e93ecd59c4547af53e5529b3fbc82
Source dataset
uspto-grants-1992_09
Patent number
US05147876

Reaction notes

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