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

HRID 2293640Notes

Reaction equation

HRID 2293640 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+]>[Pd].C1(C)C=CC=CC=1.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 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

10.43 g (0.044 mol) of 2,5-dibromopyrimidine, 10 g (0.044 mol) of 4-(phenylmethoxy)benzeneboronic acid, 0.475 g (0.00044 mol) of palladium on activated carbon (10% by weight), (0.001752 mol) of TPPTS and 9.3 g (0.0876 mol) of sodium carbonate are heated in 100 ml of toluene, 50 ml of ethanol and 30 ml of water at 80° C. for 48 hours. The palladium catalyst is subsequently separated 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 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%). ##STR26##

Workup

  1. customThe palladium catalyst is subsequently separated 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. customis dried in a high vacuum
  5. customThe crude product thus obtained
  6. customis crystallized from acetonitrile (300 ml)

Sources & evidence

ORD record
ord-22b9ceb048f0428ca9c042f3536b3f6b
Source dataset
uspto-grants-1997_11
Patent number
US05686608

Reaction notes

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