Ethanol → 2-(3-Benzyloxyphenyl)-5-bromopyrimidine

HRID 2399192Notes

Reaction equation

HRID 2399192 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH2:9]([O:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Br:8][C:5]1[CH:4]=[N:3][C:2]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([O:16][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:18]=2)=[N:7][CH:6]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343133-Benzyloxy-phenylboronic acidHCID 109555882,5-Dibromopyrimidine

Product 1

HCID 193862262-(3-Benzyloxyphenyl)-5-bromopyrimidineYield 70.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

15.00 g (63.10 mmol) of 2,5-dibromopyrimidine (for preparation see: D. W. Arantz and D. J. Brown in Journal of the Chemical Society C, 1971, p. 1889), 14.40 g (63.10 mmol) of 3-benzyloxybenzeneboronic acid, 13.40 g (126.2 mmol) of sodium carbonate and 0.73 g (0.63 mmol) of tetrakis(triphenylphosphine)palladium(0) are heated at 80° C. for 4 hours in 150 ml of toluene, 75 ml of ethanol and 50 ml of water. The reaction mixture is subsequently partitioned between ether and water, the organic phase is washed twice with sodium chloride solution, dried over sodium sulfate and evaporated, and the residue is purified by chromatography (silica gel/dichloromethane), giving 15.14 g of 5-bromo-2-(3-benzyloxyphenyl)pyrimidine. ##STR14##

Workup

  1. customThe reaction mixture is subsequently partitioned between ether and water
  2. washthe organic phase is washed twice with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customthe residue is purified by chromatography (silica gel/dichloromethane)

Sources & evidence

ORD record
ord-72290be2f4eb48ca8a986b9580a1729a
Source dataset
uspto-grants-1995_09
Patent number
US05447656

Reaction notes

Loading…