Diisobutylaluminumhydride → HCID 86682825, compound

HRID 1428178Notes

Reaction equation

HRID 1428178 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]([C:15](OCC)=[O:16])=[CH:13][N:12]=[C:11]([S:20][CH3:21])[N:10]=2)=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]([CH2:15][OH:16])=[CH:13][N:12]=[C:11]([S:20][CH3:21])[N:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86682826HCID 86682826, compound

Product 1

HCID 86682825HCID 86682825, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of ethyl 4-(4-methoxyphenyl)-2-(methylsulfanyl)pyrimidine-5-carboxylate (23.1 g) in toluene (500 mL) was added diisobutylaluminum hydride (15% toluene solution, 131 mL) at −78° C. The reaction mixture was stirred at −78° C. for 1.5 hr, and quenched with acetic acid. The reaction mixture was extracted with ethyl acetate, and the extract was washed successively with saturated aqueous sodium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (13.5 g).

Workup

  1. customquenched with acetic acid
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe extract was washed successively with saturated aqueous sodium carbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-384e557b19914515b048736b2e01baac
Source dataset
uspto-grants-2015_01
Patent number
US08937055B2

Reaction notes

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