Tributyltin Chloride → 2-(4-Trifluoromethylphenyl)-5-(tributylstannyl)pyrimidine

HRID 2105269Notes

Reaction equation

HRID 2105269 reaction equation
[Li]CCCC.Br[C:7]1[CH:8]=[N:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[N:11][CH:12]=1.[CH2:23]([Sn:27](Cl)([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH3:26]>C1COCC1>[F:20][C:19]([F:22])([F:21])[C:16]1[CH:17]=[CH:18][C:13]([C:10]2[N:9]=[CH:8][C:7]([Sn:27]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:23][CH2:24][CH2:25][CH3:26])=[CH:12][N:11]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 232970515-Bromo-2-(4-trifluoromethylphenyl)pyrimidineHCID 178418339Butyllithium

Product 1

HCID 574792592-(4-Trifluoromethylphenyl)-5-(tributylstannyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-BuLi 2.0M (ALDRICH, 0.18 ml) was added dropwise, with vigorous stirring, to a solution of 5-bromo-2-(4-trifluoromethylphenyl)pyrimidine (60 mg) in THF (2 ml) at −78° C. After stirring for 1 hour, tributyltin chloride (97 μl) was added dropwise at −78° C., under argon atmosphere. After 1 hour 30 minutes at −78° C., the reaction was quenched with 1 N NH4Cl (5 ml), diluted, extracted with ethyl acetate (3×10 ml), washed with brine, dried over MgSO4, concentrated under vacuum and purified by chromatography column using CH2Cl2-hexane 1:8 as eluent to give 75 mg of the desired product as a colorless oil.

Workup

  1. waitAfter 1 hour 30 minutes at −78° C.
  2. customthe reaction was quenched with 1 N NH4Cl (5 ml)
  3. additiondiluted
  4. extractionextracted with ethyl acetate (3×10 ml)
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under vacuum
  8. custompurified by chromatography column

Sources & evidence

ORD record
ord-1e43fcf159e442829c0498f38e4beb87
Source dataset
uspto-grants-2009_08
Patent number
US07579353B2

Reaction notes

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