Diisopropylamine → HCID 86598743, compound

HRID 419727Notes

Reaction equation

HRID 419727 reaction equation
[Li]CCCC.C(NC(C)C)(C)C.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[N:17]=[CH:16][N:15]=1.[CH:21]1([CH:24]=[O:25])[CH2:23][CH2:22]1>C1COCC1.O>[CH:21]1([CH:24]([C:19]2[C:14]([Cl:13])=[N:15][CH:16]=[N:17][C:18]=2[Cl:20])[OH:25])[CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 709434,6-DichloropyrimidineHCID 123114CyclopropanecarboxaldehydeHCID 178418339Butyllithium

Product 1

HCID 86598743HCID 86598743, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Add slowly n-BuLi (2.37 g, 36.0 mmol) to a cooled solution of diisopropylamine (3.72 g, 36.0 mmol) in 50.0 mL THF at −78° C. under nitrogen atmosphere. Stir the reaction mixture for 30 min at the same temperature, then add 4,6-dichloropyrimidine (5.0 g, 33.0 mmol) dissolved in 15 mL of THF. Stir the resultant reaction mixture for an additional 30 min at −78° C., then add cyclopropane carbaldehyde (2.58 g, 36.8 mmol). Allow the reaction mixture to warm up to room temperature. Add 50.0 mL of water and extract the organic with ethyl acetate (3×50 mL), wash with saturated aqueous sodium chloride, then dry over anhydrous sodium sulfate. Concentrate under reduced pressure under vacuum to give Cyclopropyl-(4,6-dichloro-pyrimidin-5-yl)-methanol (4.0 g, 54% yield). MS (APCI): m/z=220 [M+H]

Workup

  1. stirringStir the resultant
  2. customreaction mixture for an additional 30 min at −78° C.
  3. extractionextract the organic with ethyl acetate (3×50 mL)
  4. washwash with saturated aqueous sodium chloride
  5. dry with materialdry over anhydrous sodium sulfate
  6. concentrationConcentrate under reduced pressure under vacuum

Sources & evidence

ORD record
ord-2427426c1aa345ff9d2fe28c783cb216
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

Loading…