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

HRID 581190Notes

Reaction equation

HRID 581190 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.C1C=C(S([O-])(=O)=O)C=C(P(C2C=CC=C(S([O-])(=O)=O)C=2)C2C=CC=C(S([O-])(=O)=O)C=2)C=1.[Na+].[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(O)C>[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 10340Sodium CarbonateHCID 27343144-Benzyloxy-phenylboronic acidHCID 6099338Trisodium 3,3',3''-phosphinetriyltris(benzene-1-sulphonate)HCID 109555882,5-Dibromopyrimidine

Product 1

HCID 5640285-Bromo-2-[4-(phenylmethoxy)phenyl]pyrimidineYield 96.6%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

10.43 g (0.044 mol) of 2,5-dibromopyrimidine, 10 g (0.044 mol) of 4-(phenylmethoxy)benzeneboronic acid, 98.8 mg (0.00044 mol) of palladium(II) acetate, (0.001752 mol) of TPPTS and 9.3 g (0.0876 mol) of sodium carbonate are heated at 80° C. in 100 ml of toluene, 50 ml of ethanol and 30 ml of water for 48 hours. The palladium catalyst is subsequently separated off from the reaction mixture by filtration at 80° C. The lower aqueous 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 is dried in a high vacuum. The crude product thus obtained is crystallized from acetonitrile (300 ml), giving 14.5 g (93% yield, based on 2,5-dibromopyrimidine) of 5-bromo-2-[4-(phenylmethoxy)phenyl]-pyrimidine (content according to HPLC: 98%). ##STR18##

Workup

  1. customThe palladium catalyst is subsequently separated off from the reaction mixture by filtration at 80° C
  2. customThe lower aqueous 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. customis dried in a high vacuum
  5. customThe crude product thus obtained
  6. customis crystallized from acetonitrile (300 ml)

Sources & evidence

ORD record
ord-ba1ca0cb3a6646f6b9b90937561387b0
Source dataset
uspto-grants-1999_07
Patent number
US05919930

Reaction notes

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