Ethyl Acetate → HCID 86619520, compound

HRID 639304Notes

Reaction equation

HRID 639304 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([O:9][CH2:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:5]([NH2:8])=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:19][CH:20](Cl)[CH2:21][CH3:22].C(OCC)(=O)C>CN(C)C=O>[Br:1][C:2]1[N:3]=[C:4]([O:9][CH2:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[C:5]([N:8]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 136639211-Bromo-2-chlorobutaneHCID 86619519HCID 86619519, compound

Product 1

HCID 86619520HCID 86619520, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.544 g (0.0020 mol) 5-bromo-3-cyclopentylmethoxy-pyrazin-2-ylamine in 10 mL dimethylformamide was added 0.349 g (0.0080 mol) sodium hydride 55% in oil and the mixture was stirred at room temperature for 20 min. To the resulting suspension was added 0.345 mL (0.0030 mol) 1-bromo-2-chlorobutane and the mixture was stirred at room temperature for 2 h. The reaction mixture was partitioned between 10% aqueous citric acid and ethyl acetate. The phases were separated and the organic phase was washed with water and 10% aqueous sodium bicarbonate, dried over sodium sulfate, evaporated and the residue was purified by chromatography on silica gel with heptane:ethyl acetate=9:1 to yield 0.579 g (0.0018 mol) of the title compound as yellowish crystals melting at 54-55° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 h
  2. customThe reaction mixture was partitioned between 10% aqueous citric acid and ethyl acetate
  3. customThe phases were separated
  4. washthe organic phase was washed with water and 10% aqueous sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customthe residue was purified by chromatography on silica gel with heptane

Sources & evidence

ORD record
ord-be3e877a9d1046d6a069bd0a57528ce4
Source dataset
uspto-grants-2010_04
Patent number
US07691863B2

Reaction notes

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