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

HRID 363248Notes

Reaction equation

HRID 363248 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:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.[Pd]>[Br:8][C:5]1[CH:4]=[N:3][C:2]([C:20]2[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][CH:19]=2)=[N:7][CH:6]=1

Participants

8

Reactant 3

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

Product 1

HCID 5640285-Bromo-2-[4-(phenylmethoxy)phenyl]pyrimidine

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 104 g of 2,5-dibromopyrimidine, 100 g of 4-benzoxyphenylboronic acid, 4.75 g of Pd (10% on activated charcoal), 4.5 g of triphenylphosphene and 93 g of sodium carbonate in 1 l of toluene, 0.5 l of ethanol and 0.3 l of water is heated at 80° C. for 24 hours. After filtration, the organic phase is separated off and evaporated to dryness in vacuo. The residue is recrystallized from acetonitrile: 83 g of solids of melting point 153°-155° C.

Workup

  1. filtrationAfter filtration
  2. customthe organic phase is separated off
  3. customevaporated to dryness in vacuo
  4. customThe residue is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-5a8242bfa432484d87da14a66bb1736e
Source dataset
uspto-grants-1999_02
Patent number
US05872301

Reaction notes

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