Tetrahydrofuran → 2-{4-(1-Decenyl)-phenyl}-5-hydroxypyrimidine

HRID 378190Notes

Reaction equation

HRID 378190 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([OH:14])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O1[CH2:21][CH2:20][CH2:19][CH2:18]1>>[CH:18]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([OH:14])=[CH:10][N:9]=2)=[CH:4][CH:3]=1)=[CH:19][CH2:20][CH2:21][CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 6199082-(4-Bromophenyl)pyrimidin-5-ol

Product 1

HCID 540193422-{4-(1-Decenyl)-phenyl}-5-hydroxypyrimidineYield 75%

Procedure

After replacing inner atmosphere of a four-necked flask equipped with a stirring device and a thermometer with nitrogen gas, the flask was charged with 1.26 g (5 mmol) of 2-(4-bromophenyl)-5-hydroxy-pyrimidine, 0.01 g (0.008 mmol) of tetrakis-triphenylphosphine-palladium, 0.6 g (15 mmol) of sodium hydroxide and 20 ml of tetrahydrofuran. Then, 19.5 ml of a solution prepared by dissolving 7.5 mmol of E-1-nonenylcatecholborane, prepared in the same manner as in Example 2, in tetrahydrofuran was dropwise added at room temperature. The resulting mixture was heated under reflux with stirring for 7 hours. After cooling the mixture to room temperature, the mixture was extracted with 30 ml of toluene, and the organic layer was twice washed with each 10 ml portion of saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent, purification of the residue by silica gel column chromatography gave 1.16 g (yield 75%) of 2-{4-(1-decenyl)-phenyl}-5-hydroxypyrimidine.

Workup

  1. customequipped with a stirring device
  2. dissolutionby dissolving 7.5 mmol of E-1-nonenylcatecholborane
  3. additionwas dropwise added at room temperature
  4. temperatureThe resulting mixture was heated
  5. temperatureunder reflux
  6. extractionthe mixture was extracted with 30 ml of toluene
  7. washthe organic layer was twice washed with each 10 ml portion of saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationAfter distilling off
  10. customthe solvent, purification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-626833c1a1c3451e913831b3c29a3c2e
Source dataset
uspto-grants-2000_02
Patent number
US06030546

Reaction notes

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