Tert-Butylamine → 5-Bromo-N-tert-butyl-2-chloropyrimidin-4-amine

HRID 82166Notes

Reaction equation

HRID 82166 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Br:6][C:7]1[C:8](Cl)=[N:9][C:10]([Cl:13])=[N:11][CH:12]=1.C(N(CC)CC)C>C(#N)C>[Br:6][C:7]1[C:8]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N:9][C:10]([Cl:13])=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 790766715-Bromo-N-tert-butyl-2-chloropyrimidin-4-amineYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butylamine (5.28 g, 72 mmol) was added to 5-bromo-2,4-dichloropyrimidine (15 g, 66 mmol) and triethylamine (19.9 g, 197 mmol) in acetonitrile (450 mL) at room temperature and the mixture was stirred at room temperature for 16 hours. Then the mixture was evaporated in vacuo and the crude residue was partitioned between EtOAc (450 mL) and water (400 mL). The organic layer was separated, washed with brine (400 mL) then dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:EtOAc 88:12) to afford the title compound as a yellow oil in 52% yield, 8.8 g.

Workup

  1. customThen the mixture was evaporated in vacuo
  2. customthe crude residue was partitioned between EtOAc (450 mL) and water (400 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (400 mL)
  5. dry with materialthen dried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (hexane:EtOAc 88:12)

Sources & evidence

ORD record
ord-1bdd55552f8445d6b076c2c4b1d91528
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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