Sodium Carbonate → 5-Bromo-2-(4-trifluoromethylphenyl)pyrimidine

HRID 2105268Notes

Reaction equation

HRID 2105268 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:14]2[CH:15]=[CH:16][C:11]([C:10]([F:21])([F:20])[F:9])=[CH:12][CH:13]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 70066515-Bromo-2-iodopyrimidine

Product 1

HCID 232970515-Bromo-2-(4-trifluoromethylphenyl)pyrimidineYield 60.2%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

5-bromo-2-iodopyrimidine (250 mg), 4-trifluoromethylphenylboronic acid (167 mg), bis(triphenylphosphine)palladium(II) chloride (22 mg) and Na2CO3 (2.1 ml, 1M in H2O) in argon saturated acetonitrile (2.1 ml) was heated under microwave conditions (150° C., 10 minutes). The conversion was monitored and analyzed by HPLC. The crude reaction mixture was concentrated to dryness, then diluted with CH2Cl2, washed with water (3×10 ml), dried over Na2SO4, concentrated under vacuum and purified by chromatography column using CH2Cl2-hexane 1:10 as eluent to give 160 mg of the desired product as a white solid.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated to dryness
  3. additiondiluted with CH2Cl2
  4. washwashed with water (3×10 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. custompurified by chromatography column

Sources & evidence

ORD record
ord-9e44df1191674887be632656415a2350
Source dataset
uspto-grants-2009_08
Patent number
US07579353B2

Reaction notes

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