Carbon Dioxide → [Rac]-1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethanol

HRID 1242324Notes

Reaction equation

HRID 1242324 reaction equation
[C:1](=O)=O.[CH:4]1([C:7]2[C:12]([CH:13]=[O:14])=[CH:11][N:10]=[C:9]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[N:8]=2)[CH2:6][CH2:5]1.C[Mg]Br>C1COCC1.CCOCC>[CH:4]1([C:7]2[C:12]([CH:13]([OH:14])[CH3:1])=[CH:11][N:10]=[C:9]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:17][CH:16]=3)[N:8]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 219356514-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 21935779[Rac]-1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a dry ice chilled solution of 0.75 g (2.57 mmol) 4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carbaldehyde in 5 ml THF was dropped a solution of 1.11 ml (3.33 mmol) 3M methylmagnesium bromide in 2.5 ml THF. The reaction mixture was allowed to warm to RT and it was stirred for 15 min at this temperature. The reaction mixture was then taken up in ether and washed with 1N HCl and water. The crude product was purified by chromatography over silica gel with AcOEt/dichloromethane 1:6, to give 384 mg of pure [rac]-1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethanol.

Workup

  1. washwashed with 1N HCl and water
  2. customThe crude product was purified by chromatography over silica gel with AcOEt/dichloromethane 1:6

Sources & evidence

ORD record
ord-fab5ad92c3574efa9cc13e890165f851
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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