Diisopropylamine → HCID 67462540, compound

HRID 2202782Notes

Reaction equation

HRID 2202782 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH2:13]([N:20]1[CH:25]2[CH2:26][CH2:27][CH:21]1[CH2:22][C:23](=[O:28])[CH2:24]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Br:29][C:30]1[CH:31]=[N:32][CH:33]=[N:34][CH:35]=1>C1COCC1.C(OCC)(=O)C.O>[CH2:13]([N:20]1[CH:21]2[CH2:27][CH2:26][CH:25]1[CH2:24][C:23]([C:31]1[C:30]([Br:29])=[CH:35][N:34]=[CH:33][N:32]=1)([OH:28])[CH2:22]2)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 783445-BromopyrimidineHCID 1198468-Benzyl-8-azabicyclo(3.2.1)octan-3-oneHCID 178418339Butyllithium

Product 1

HCID 67462540HCID 67462540, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

n-Butyl lithium (2.5M, 1.2 mL, 3.00 mmol) was added dropwise to a solution of diisopropylamine (0.406 mL, 3.0 mmol) in THF (5 mL) at 0° C. under nitrogen and stirred for 30 minutes. The mixture was then added to a solution of 8-benzyl-8-aza-bicyclo[3.2.1]octan-3-one (0.64 g, 3.0 mmol) and 5-bromopyrimidine (0.477 g, 3.0 mmol) in THF (5 mL) and stirred at 0° C. for 1 hour. Water and ethyl acetate were added, the organics separated, dried over sodium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 20-50% ethyl acetate/cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound. LCMS m/z 374.2 [M+H]+. R.T.=2.06 min (Analytical Method 3).

Workup

  1. stirringstirred at 0° C. for 1 hour
  2. dry with materialthe organics separated, dried over sodium sulphate
  3. filtrationfiltered
  4. customthe solvent removed by evaporation under vacuum
  5. customThe residue was purified by flash chromatography on silica eluting with 20-50% ethyl acetate/cyclohexane
  6. additionThe fractions containing the desired product
  7. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-48c08f47c11243a3822981d4000f570a
Source dataset
uspto-grants-2016_06
Patent number
US09365564B2

Reaction notes

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