Hydrochloric Acid → (4-Bromo-phenyl)-(8-pyrimidin-2-yl-8-aza-bicyclo[3.2.1]oct-3-yl)-methanone

HRID 1619220Notes

Reaction equation

HRID 1619220 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:23]C)=[C:9]2[CH2:15][CH:14]3[N:16]([C:17]4[N:22]=[CH:21][CH:20]=[CH:19][N:18]=4)[CH:11]([CH2:12][CH2:13]3)[CH2:10]2)=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:9]2[CH2:15][CH:14]3[N:16]([C:17]4[N:18]=[CH:19][CH:20]=[CH:21][N:22]=4)[CH:11]([CH2:12][CH2:13]3)[CH2:10]2)=[O:23])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 687002943-[(4-Bromo-phenyl)-methoxy-methylene]-8-pyrimidin-2-yl-8-aza-bicyclo[3.2.1]octane

Product 1

HCID 68699864(4-Bromo-phenyl)-(8-pyrimidin-2-yl-8-aza-bicyclo[3.2.1]oct-3-yl)-methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[(4-bromo-phenyl)-methoxy-methylene]-8-pyrimidin-2-yl-8-aza-bicyclo[3.2.1]octane (2.44 g, 6.32 mmol), aqueous HCl (10.5 ml, 6N) and THF (50 ml) was stirred at room temperature overnight. The mixture was added by saturated aq. NaHCO3 until bubbling was gone. The mixture was diluted with ethyl acetate and the organic phase was dried over MgSO4 and concentrated. ISCO was used to do purification and (4-bromo-phenyl)-(8-pyrimidin-2-yl-8-aza-bicyclo[3.2.1]oct-3-yl)-methanone was obtained as white solid (2.16 g, 92%). MS (M+1)=374. 1H NMR (CDCl3) 8.33 (d, J=12 Hz 2H), 7.84 (d, J=13 Hz 2H), 7.62 (d, J=13 Hz 2H), 6.51 (t, J=12 Hz 1H), 4.87 (m, 2H), 3.90 (m, 1H), 2.23 (m, 2H), 2.08 (m, 2H), 1.97 (m, 2H), 1.72 (m, 2H).

Workup

  1. customuntil bubbling
  2. additionThe mixture was diluted with ethyl acetate
  3. dry with materialthe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. custompurification

Sources & evidence

ORD record
ord-6e7dbd0950534212aba9e920b8bfd5ed
Source dataset
uspto-grants-2014_07
Patent number
US08772291B2

Reaction notes

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