Water → Ethyl 3-(6-(((tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)-3-cyclopropylacrylate

HRID 1049494Notes

Reaction equation

HRID 1049494 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[Si:17]([O:34][CH2:35][C:36]1[N:41]=[CH:40][N:39]=[C:38]([C:42]([CH:44]2[CH2:46][CH2:45]2)=O)[CH:37]=1)([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C1COCC1>[Si:17]([O:34][CH2:35][C:36]1[N:41]=[CH:40][N:39]=[C:38]([C:42]([CH:44]2[CH2:45][CH2:46]2)=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:37]=1)([C:30]([CH3:31])([CH3:32])[CH3:33])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 131736018(6-(((Tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)(cyclopropyl)methanone

Product 1

HCID 131736019Ethyl 3-(6-(((tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)-3-cyclopropylacrylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, ethyl diethylphosphonoacetate (16.8 mL) was added to a suspension of 60% sodium hydride (3.01 g) in THF (100 mL) at 0° C., and the mixture was stirred for 5 min. To the reaction mixture was added (6-(((tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)(cyclopropyl)methanone (entire amount) obtained in Example 29, step F, at 0° C., and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (7.26 g) as a yellow oil.

Workup

  1. customobtained in Example 29, step F, at 0° C.
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3eb73adbe0c54afbb1be7ce1a23bd276
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

Loading…