Diisobutylaluminum hydride → HCID 21935665, compound

HRID 1242350Notes

Reaction equation

HRID 1242350 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH:22]2[CH2:24][CH2:23]2)=[N:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[N:10][CH:11]=1)=O)C.CC(C[AlH]CC(C)C)C>C1COCC1>[CH:22]1([C:7]2[C:6]([CH2:4][OH:3])=[CH:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=3)[N:8]=2)[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 67072262HCID 67072262, compound

Product 1

HCID 21935665HCID 21935665, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.250 g (3.717 mmol) of the above prepared 4-cyclopropyl-2-(3-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid ethyl ester in 19 ml of abs. THF was cooled down to −15° C. and reacted with 11.2 ml of DIBAL-H-solution (1.0 M in toluene, 3 eq.) for 1/2 h. Careful quenching with ice/HCl dil., twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents left a crude product which was purified by flash chromatography (SiO2, hexane/AcOEt=1/1l) to yield finally 1.096 g of the title compound as white solid of mp. 108–09° C.

Workup

  1. customCareful quenching with ice/HCl dil., twofold extraction with AcOEt
  2. washwashing with water
  3. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  4. waitleft a crude product which
  5. customwas purified by flash chromatography (SiO2, hexane/AcOEt=1/1l)

Sources & evidence

ORD record
ord-700a6c671422465bac87edfe458f867a
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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