Sodium hydride → HCID 67630337, compound

HRID 861399Notes

Reaction equation

HRID 861399 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[C:10]([CH:11]([C:13]2[C:14]([CH3:19])=[N:15][CH:16]=[N:17][CH:18]=2)[OH:12])=[CH:9][N:8]=[CH:7][N:6]=1)[CH3:4].[C:20](Cl)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22]>C1COCC1>[CH2:3]([C:5]1[C:10]([CH:11]([C:13]2[C:14]([CH3:19])=[N:15][CH:16]=[N:17][CH:18]=2)[O:12][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:9][N:8]=[CH:7][N:6]=1)[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62493Pivaloyl chlorideHCID 19702786HCID 19702786, compound

Product 1

HCID 67630337HCID 67630337, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3.2 mg of oil-free NaH was added 26 mg of 1-(4-ethylpyrimidin-5-yl)-1-(4-methylpyrimidin-5-yl)methanol in 1 ml THF at -30° C., followed by addition of 15 mg of pivaloyl chloride. After warming to room temperature and stirring for 1.5 hours, the reaction was quenched with 1 ml H2O and extracted with ether (3 times). The combined organics were washed with brine, dried (MgSO4) and evaporated to yield 30.7 mg of 1-(4-ethylpyrimidin-5-yl)-1-(4-methylpyrimidin-5-yl)-1-trimethylacetoxymethane as a yellow oil.

Workup

  1. customthe reaction was quenched with 1 ml H2O
  2. extractionextracted with ether (3 times)
  3. washThe combined organics were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-a937adffbee2430d81874daede16fc3b
Source dataset
uspto-grants-1998_02
Patent number
US05714438

Reaction notes

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