1-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-4-(2-fluoro-phenyl)-1H-pyrimidin-2-one → 4-(2-Fluoro-phenyl)-1-(4-hydroxy-butyl)-1H-pyrimidin-2-one

HRID 1514434Notes

Reaction equation

HRID 1514434 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])=[N:13][C:12]1=[O:24])(C)(C)C>Cl.O1CCOCC1>[F:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:14]1[CH:15]=[CH:16][N:11]([CH2:10][CH2:9][CH2:8][CH2:7][OH:6])[C:12](=[O:24])[N:13]=1

Participants

4

Reactant 1

HCID 592427901-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-4-(2-fluoro-phenyl)-1H-pyrimidin-2-one

Product 1

HCID 592427824-(2-Fluoro-phenyl)-1-(4-hydroxy-butyl)-1H-pyrimidin-2-oneYield 100.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

1-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-4-(2-fluoro-phenyl)-1H-pyrimidin-2-one (370 mg, 0.98 mmol) was dissolved in 4N HCl in dioxane (15 ml). The mixture was stirred at room temperature for 15 minutes, then basified with 30% NH4OHaq and finally extracted with DCM. The organic layer was dried (Na2SO4), filtered and evaporated, to give 258 mg of the title compound as a yellow solid (95% yield).

Workup

  1. extractionfinally extracted with DCM
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-1464adfe218b436e985926859976efae
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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