Benzyl Alcohol → 2-(Benzyloxy)-5-bromopyrimidine

HRID 661467Notes

Reaction equation

HRID 661467 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[N:10][C:11](Cl)=[N:12][CH:13]=1.[CH2:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C)C=O>[CH2:15]([O:22][C:11]1[N:10]=[CH:9][C:8]([Br:7])=[CH:13][N:12]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 6066655-Bromo-2-chloropyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 425530552-(Benzyloxy)-5-bromopyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium tert-butoxide (6.96 g) was added to a solution of 5-bromo-2-chloro-pyrimidine (10 g) and benzyl alcohol (6.4 ml) in N,N-dimethylformamide (140 ml) and the mixture was stirred at room temperature for 1.5 hours. Water was added to the mixture and the precipitated solid was collected by filtration, washed with methanol, dried to give the titled compound (10.6 g). MS (m/z): 265/267 [M+H]+.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with methanol
  3. customdried

Sources & evidence

ORD record
ord-75fac8084e064c31a3e60de3965adb11
Source dataset
uspto-grants-2011_12
Patent number
US08084611B2

Reaction notes

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