Allylamine → HCID 86637340, compound

HRID 2189297Notes

Reaction equation

HRID 2189297 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH2:10]([NH2:13])[CH:11]=[CH2:12].C(N(C(C)C)CC)(C)C>C(O)C>[CH2:10]([NH:13][C:3]1[C:2]([Br:1])=[CH:7][N:6]=[C:5]([Cl:8])[N:4]=1)[CH:11]=[CH2:12]

Participants

5

Reactant 3

HCID 7853AllylamineHCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 86637340HCID 86637340, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-bromo-2,4-dichloropyrimidine (5.0 g, 22 mmol), allylamine (1.98 mL, 26.4 mmol), and diisopropylethylamine (5.6 mL, 33.0 mmol) are stirred in ethanol (100 mL) at 50° C. overnight. The solvent is removed in vacuo and the residue is partitioned between ethyl acetate and saturated aqueous ammonium chloride solution. The organic layer is washed with brine, dried over anhydrous sodium sulfate and evaporated to provide Allyl-(5-bromo-2-chloro-pyrimidin-4-yl)-amine as a white crystalline solid (89%), which is used without further purification.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between ethyl acetate and saturated aqueous ammonium chloride solution
  3. washThe organic layer is washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-d406976bc6ae4c33b42f5e51d19ce8a7
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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