2-(4-Trifluoromethyl-phenyl)-pyrimidine-5-carbaldehyde → Cyclopentyl(2-(4-(trifluoromethyl)phenyl)pyrimidin-5-yl)methanol

HRID 2173889Notes

Reaction equation

HRID 2173889 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[CH:19]1([Mg]Br)[CH2:23][CH2:22][CH2:21][CH2:20]1>C1COCC1>[CH:19]1([CH:15]([C:12]2[CH:13]=[N:14][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:17])[F:18])=[CH:8][CH:7]=3)=[N:10][CH:11]=2)[OH:16])[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 219363042-(4-Trifluoromethyl-phenyl)-pyrimidine-5-carbaldehydeHCID 178419650HCID 178419650, compound

Product 1

HCID 67980743Cyclopentyl(2-(4-(trifluoromethyl)phenyl)pyrimidin-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a −78° C. solution of 2-(4-(trifluoromethyl)phenyl)pyrimidine-5-carbaldehyde (1.0 g, 3.96 mmol) in THF (6 mL) was added cyclopentylmagnesium bromide (2.97 mL of a 2.0M solution in THF, 5.95 mmol). The solution was stirred at 0° C. for two hours. The mixture was quenched with saturated aqueous NH4Cl, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography to give cyclopentyl(2-(4-(trifluoromethyl)phenyl)pyrimidin-5-yl)methanol (1.0 g) as a red oil.

Workup

  1. customThe mixture was quenched with saturated aqueous NH4Cl
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6fe3991a8dbe4a14b318fd63d422a01d
Source dataset
uspto-grants-2015_06
Patent number
US09056834B2

Reaction notes

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