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

HRID 1496912Notes

Reaction equation

HRID 1496912 reaction equation
I[C:2]1[N:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[F:9][C:10]([F:26])([F:25])[O:11][C:12]1[CH:17]=[CH:16][C:15](C2C=CC(O)=CC=2)=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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>[Br:8][C:5]1[CH:4]=[N:3][C:2]([C:15]2[CH:14]=[CH:13][C:12]([O:11][C:10]([F:9])([F:25])[F:26])=[CH:17][CH:16]=2)=[N:7][CH:6]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 70066515-Bromo-2-iodopyrimidineHCID 120087344-(4-Trifluoromethoxyphenyl)phenol

Product 1

HCID 574792805-Bromo-2-[4-(trifluoromethoxy)phenyl]pyrimidineYield 75.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 5-bromo-2-iodopyrimidine (88) (1.50 g, 5.27 mmol), 4-(trifluoromethoxy)phenylboronic acid (44) (1.185 g, 5.75 mmol) and Na2CO3 (1.11 g, 10.5 mmol) in toluene (120 mL) and water (15 mL) was purged with N2. Pd(PPh3)4 (60 mg, 0.05 mmol) was added and the mixture was refluxed under N2 for 17.5 h, then partitioned between EtOAc and water. Column chromatography of the organic portion on silica gel (eluting with 4:1 hexanes/CH2Cl2) gave 5-bromo-2-[4-(trifluoromethoxy)phenyl]pyrimidine (89) (1.264 g, 75%) as a white solid: mp 107-108° C.; 1H NMR (CDCl3) δ 8.83 (s, 2H), 8.46 (d, J=9.0 Hz, 2H), 7.31 (d, J=9.0 Hz, 2H). APCI MS m/z 319, 321 [M+H]+.

Workup

  1. customwas purged with N2
  2. temperaturethe mixture was refluxed under N2 for 17.5 h
  3. custompartitioned between EtOAc and water

Sources & evidence

ORD record
ord-733afcbff2ad464b97a894ae93ac2805
Source dataset
uspto-grants-2015_12
Patent number
US09198913B2

Reaction notes

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