Sodium Carbonate → 2-[4-(Benzyloxy)-2,3-difluorophenyl]-5-bromopyrimidine

HRID 376761Notes

Reaction equation

HRID 376761 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)=[C:19]([F:26])[C:18]=1[F:27])[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.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>[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[N:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=2)=[C:19]([F:26])[C:18]=1[F:27])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 109555882,5-DibromopyrimidineHCID 152187534-Benzyloxy-2,3-difluorobenzeneboronic acid

Product 1

HCID 178694022-[4-(Benzyloxy)-2,3-difluorophenyl]-5-bromopyrimidineYield 26.5%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A reaction of 14 mmol of 2,5-dibromopyrimidine, 17 mmol of 4-benzyloxy-2,3-difluorophenylboronic acid, 34 mmol of sodium carbonate and 0.14 mmol of tetrakis(triphenylphosphine)palladium(0) in 100 ml of toluene, 50 ml of ethanol and 50 ml of water is carried out analogously to the procedure indicated for precursor 3. Purification by recrystallization from 2-propanol gives 1.4 g (26%) of a colorless solid, m.p. 138° C.

Workup

  1. customPurification
  2. customby recrystallization from 2-propanol

Sources & evidence

ORD record
ord-bf5b4f514297404a9eba262211402890
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

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