Diisobutylaluminum hydride → 2-[4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethanol

HRID 1727009Notes

Reaction equation

HRID 1727009 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[C:6]([CH:21]2[CH2:23][CH2:22]2)=[N:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:9][CH:10]=1.ClCC1C(C2CC2)=NC(C2C=CC(C(F)(F)F)=CC=2)=NC=1.CC(C[AlH]CC(C)C)C>C1COCC1>[CH:21]1([C:6]2[C:5]([CH2:4][CH2:3][OH:2])=[CH:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:15][CH:16]=3)[N:7]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 219359605-Chloromethyl-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidineHCID 69036962[4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-acetic acid methyl ester

Product 1

HCID 222508192-[4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.60 g (1.78 mmol) of [4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-acetic acid methyl ester (prepared from 5-chloromethyl-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine (example 9E]) in analogy to the sequences described in examples 4H] to 4J]) was dissolved in 10 ml of abs. THF and cooled down to 0° C. It was then reacted with 3.18 nml of DIBAL-H-solution (1.2 M in toluene) and the mixture stirred for 2 h at room temperature. Careful quenching with ice/THF/H2O, twofold extraction with AcOEt, washing with diluted HCl solution and brine, drying over sodium sulfate, and evaporation of the solvents left a crude product which was purified by crystallization from dichloromethane/n-heptane to deliver finally 0.53 g of the title compound as light yellow solid.

Workup

  1. dissolutionwas dissolved in 10 ml of abs
  2. customCareful quenching with ice/THF/H2O, twofold extraction with AcOEt
  3. washwashing with diluted HCl solution and brine
  4. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  5. waitleft a crude product which
  6. customwas purified by crystallization from dichloromethane/n-heptane

Sources & evidence

ORD record
ord-d751c4329f9f488eb73e2ff098c92e5d
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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