5-Bromo-2,4-dichloropyrimidine → Bicyclo[1.1.1]pent-1-yl-(5-bromo-2-chloro-pyrimidin-4-yl)-amine

HRID 82298Notes

Reaction equation

HRID 82298 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[C:10]12([NH2:15])[CH2:14][CH:12]([CH2:13]1)[CH2:11]2>C(#N)C>[C:10]12([NH:15][C:3]3[C:2]([Br:1])=[CH:7][N:6]=[C:5]([Cl:8])[N:4]=3)[CH2:14][CH:12]([CH2:13]1)[CH2:11]2

Participants

4

Reactant 2

HCID 2899735-Bromo-2,4-dichloropyrimidineHCID 11469065Bicyclo(1.1.1)pentan-1-amine

Product 1

HCID 86672128Bicyclo[1.1.1]pent-1-yl-(5-bromo-2-chloro-pyrimidin-4-yl)-amineYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-Bromo-2,4-dichloro-pyrimidine (6 g, 26.3 mmol) and bicyclo[1.1.1]pent-1-ylamine (4.7 g, 39.5 mmol) in acetonitrile (60 mL), was added TEA (16.5 mL, 118 mmol), and the mixture was stirred at 25° C. for 18 hours. The volatiles were removed in vacuo and the residue partitioned between water and EtOAc. The organic phase was dried (Na2SO4) and evaporated in vacuo. Purification by column chromatography on silica gel (EtOAc:Hexane 1:99) afforded the title compound as a white solid in 82% yield, 4.8 g.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue partitioned between water and EtOAc
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated in vacuo
  5. customPurification by column chromatography on silica gel (EtOAc:Hexane 1:99)

Sources & evidence

ORD record
ord-5986d92af0194edf8983e02e6df604c3
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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