Ammonium Chloride → HCID 67463235, compound

HRID 2202800Notes

Reaction equation

HRID 2202800 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[N:11][CH:12]=1.[C:13]([O:17][C:18]([N:20]1[CH:25]2[CH2:26][CH2:27][CH:21]1[CH2:22][C:23](=[O:28])[CH2:24]2)=[O:19])([CH3:16])([CH3:15])[CH3:14].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[C:13]([O:17][C:18]([N:20]1[CH:25]2[CH2:26][CH2:27][CH:21]1[CH2:22][C:23]([OH:28])([C:7]1[CH:8]=[N:9][CH:10]=[N:11][CH:12]=1)[CH2:24]2)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 783445-BromopyrimidineHCID 2794767tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylateHCID 178418339Butyllithium

Product 1

HCID 67463235HCID 67463235, compoundYield 15.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

n-Butyl lithium (2.5 M, 1.8 mL, 4.5 mmol) was added dropwise to a solution of 5-bromo-pyrimidine (0.668 g, 4.2 mmol) in THF (10 mL), under nitrogen at −78° C. and stirred for 1 hour. 3-Oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (0.675 g, 3.0 mmol) in THF (5 mL) was added dropwise at −78° C. and the reaction mixture warmed to room temperature over 1 hour. Saturated aqueous ammonium chloride and ethyl acetate were added, the organics separated, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 10% methanol/ethyl acetate. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.14 g). LCMS m/z 306 [M+H]+. R.T.=2.89 min (Analytical Method 3).

Workup

  1. dry with materialthe organics separated, dried over magnesium sulphate
  2. filtrationfiltered
  3. customthe solvent removed by evaporation under vacuum
  4. customThe residue was purified by flash chromatography on silica eluting with 10% methanol/ethyl acetate
  5. additionThe fractions containing the desired product
  6. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-4e58084d17774ee388474e80c29b4e85
Source dataset
uspto-grants-2016_06
Patent number
US09365564B2

Reaction notes

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