1-[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]-6-trimethylsilyl-5-hexyn-1-one → 1-[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]-5-hexyn-1-one

HRID 2082032Notes

Reaction equation

HRID 2082032 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:7]([C:16](=[O:26])[CH2:17][CH2:18][CH2:19][C:20]#[C:21][Si](C)(C)C)[N:6]=1)([CH3:4])[CH3:3].O.O.[F-].[K+]>CN(C)C=O>[CH3:4][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[N:8]=[C:7]([C:16](=[O:26])[CH2:17][CH2:18][CH2:19][C:20]#[CH:21])[N:6]=1)([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 104520651-[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]-6-trimethylsilyl-5-hexyn-1-oneHCID 23708904Potassium fluoride dihydrate

Product 1

HCID 104026731-[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]-5-hexyn-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-[4,6-bis(1,1-dimethylethyl)-5-hydroxypyrimidin-2-yl]-6-trimethylsilyl-5-hexyn-1-one (0.87 g, 2.3 mmol), Example 8, and potassium fluoride dihydrate (0.91 g, 9.7 mmol) in N,N-dimethylformamide (12 mL) is warmed to 50° C. After stirring for 47 hours at 50° C., the solvent is removed under vacuum and the organic residue is diluted with water. This mixture is extracted with ethyl acetate and the combined extracts are washed with saturated aqueous ammonium chloride solution and brine. The organic is concentrated under vacuum and the organic residue purified by flash chromatorgraphy (SiO2, 20% ethyl acetate (hexane) followed by recrystallization from methanol and water to give 0.48 g (68%) of the title compound), mp 64°-66° C.

Workup

  1. customthe solvent is removed under vacuum
  2. additionthe organic residue is diluted with water
  3. extractionThis mixture is extracted with ethyl acetate
  4. washthe combined extracts are washed with saturated aqueous ammonium chloride solution and brine
  5. concentrationThe organic is concentrated under vacuum
  6. customthe organic residue purified by flash chromatorgraphy (SiO2, 20% ethyl acetate (hexane) followed by recrystallization from methanol and water to give 0.48 g (68%) of the title compound), mp 64°-66° C.

Sources & evidence

ORD record
ord-0d36db042726453b98e1b22d12424a22
Source dataset
uspto-grants-1993_02
Patent number
US05187175

Reaction notes

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