Ethanol → 5-Bromo-2-[4-(phenylmethoxy)phenyl]pyrimidine

HRID 1078799Notes

Reaction equation

HRID 1078799 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9]1([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Br:8][C:5]1[CH:4]=[N:3][C:2]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH2:15][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:18][CH:19]=2)=[N:7][CH:6]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343144-Benzyloxy-phenylboronic acidHCID 109555882,5-Dibromopyrimidine

Product 1

HCID 5640285-Bromo-2-[4-(phenylmethoxy)phenyl]pyrimidineYield 100.4%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 23938PalladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

104.25 g (0.438 mol) of 2,5-dibromopyrimidine, 100.00 g (0.438 mol) of 4-(phenylmethoxy)benzeneboronic acid, 4.75 g (0.00438 mol) of palladium (10%) on activated carbon, 4.50 g (0.01752 mol) of triphenylphosphine and 93.00 g (0.876 mol) of sodium carbonate are heated in 1000 ml of toluene, 500 ml of ethanol and 300 ml of water for 24 hours at 80° C. The palladium catalyst is subsequently separated off from the reaction mixture at 80° C. by filtration. The aqueous lower phase of the reaction mixture is separated off at 80° C., before the organic phase is freed of the solvents on a rotary evaporator and dried in a high vacuum. The crude product thus obtained is recrystallized from acetonitrile (3000 ml), giving 150.07 g (97% yield, based on 2,5-dibromopyridine) of 5-bromo-2-[4-(phenylmethoxy)phenyl]pyrimidine (purity according to HPLC: 98%). ##STR4## mp.: 153°-155° C.

Workup

  1. customThe palladium catalyst is subsequently separated off from the reaction mixture at 80° C. by filtration
  2. customThe aqueous lower phase of the reaction mixture is separated off at 80° C., before the organic phase
  3. customis freed of the solvents on a rotary evaporator
  4. customdried in a high vacuum
  5. customThe crude product thus obtained
  6. customis recrystallized from acetonitrile (3000 ml)

Sources & evidence

ORD record
ord-7522b677a89d4482841967e4c53bf8fc
Source dataset
uspto-grants-1996_08
Patent number
US05550236

Reaction notes

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