Water → 2-(4-(Octyloxy)phenyl)pyrimidin-5-ol

HRID 1755624Notes

Reaction equation

HRID 1755624 reaction equation
C([O:8][C:9]1[CH:10]=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[N:13][CH:14]=1)C1C=CC=CC=1.[H-].[Na+].[CH2:24](Br)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].O>CN(C)C=O>[OH:8][C:9]1[CH:14]=[N:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:19][CH:20]=2)=[N:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 1357441904-[5-(Benzyloxy)pyrimidin-2(1H)-ylidene]cyclohexa-2,5-dien-1-one

Product 1

HCID 144963952-(4-(Octyloxy)phenyl)pyrimidin-5-olYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-Benzyloxy-2- (4-hydroxyphenyl) pyrimidine (2 g, 0.0072 moles, Example 30) was dissolved in 15 ml of N,N-dimethylformamide in a 50 ml flask and 0.2 g of dry sodium hydride was added. After stirring the mixture for 15 minutes, 1.39 g (0.0072 moles) of octylbromide was added and the mixture was heated to 100° C. for 2 hours. Upon cooling to room temperature, 15 ml of water was added. The resulting solid was collected by filtration and the solid was then slurried in boiling methanol, cooled to room temperature, and again collected by filtration. The solid was hydrogenated on a Parr Hydrogenator with catalytic 10% palladium on carbon in tetrahydrofuran under 413.7 kPa hydrogen pressure for about 18 hours. When the hydrogenation was complete, the catalyst was removed by filtration, and the solvent was removed on a rotary evaporator to yield 1.62 g (75% yield) of 5-hydroxy-2-(4-(octyloxy)phenyl)pyrimidine.

Workup

  1. temperatureUpon cooling to room temperature
  2. filtrationThe resulting solid was collected by filtration
  3. temperaturecooled to room temperature
  4. filtrationagain collected by filtration
  5. waitThe solid was hydrogenated on a Parr Hydrogenator with catalytic 10% palladium on carbon in tetrahydrofuran under 413.7 kPa hydrogen pressure for about 18 hours
  6. customthe catalyst was removed by filtration
  7. customthe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-e5dac9e302534734bd9c2879e59ad11c
Source dataset
uspto-grants-1995_08
Patent number
US05437812

Reaction notes

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