Diisobutylaluminumhydride → HCID 46941731, compound

HRID 1428175Notes

Reaction equation

HRID 1428175 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14](OCC)=[O:15])=[CH:12][N:11]=[C:10]([S:19][CH3:20])[N:9]=2)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH2:14][OH:15])=[CH:12][N:11]=[C:10]([S:19][CH3:20])[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 46941730HCID 46941730, compound

Product 1

HCID 46941731HCID 46941731, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of ethyl 4-(4-fluorophenyl)-2-(methylsulfanyl)pyrimidine-5-carboxylate (21.0 g) in toluene (500 mL) was added diisobutylaluminum hydride (15% toluene solution, 124 mL) at −78° C. The reaction mixture was stirred at −78° C. for 1.5 hr, and the reaction was 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 (10.3 g).

Workup

  1. customthe reaction was quenched 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-2ada9469bbae4249aed7bc5911309573
Source dataset
uspto-grants-2015_01
Patent number
US08937055B2

Reaction notes

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