Sodium Bicarbonate → 8-(2-Methylbenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyrazine

HRID 4302Notes

Reaction equation

HRID 4302 reaction equation
C(=O)(O)[O-].[Na+].[NH2:6][C:7]1[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[N:11][CH:10]=[CH:9][N:8]=1.S(O[CH:27]([CH2:31][C:32]#[CH:33])[C:28](=O)[CH3:29])(C)(=O)=O>C(O)C>[CH3:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][O:13][C:12]1[C:7]2[N:8]([C:27]([CH2:31][C:32]#[CH:33])=[C:28]([CH3:29])[N:6]=2)[CH:9]=[CH:10][N:11]=1

Participants

5

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 138259752-Amino-3-(2-methylbenzyloxy)pyrazineHCID 143683463-Mesyloxy-5-hexyn-2-one

Product 1

HCID 138259678-(2-Methylbenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyrazineYield 3.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium bicarbonate (2.73 g) was added to a solution of 2-amino-3-(2-methylbenzyloxy)pyrazine (3.5 g) and 3-mesyloxy-5-hexyn-2-one (6.18 g) in ethanol (35 ml) and the mixture was refluxed for 12 hours. The mixture was poured into an aqueous solution of sodium bicarbonate and extracted with chloroform. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (200 g) with a mixture of chloroform and methanol (50:1) as an eluent to give 8-(2-methylbenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyrazine (0.182 g).

Workup

  1. temperaturethe mixture was refluxed for 12 hours
  2. extractionextracted with chloroform
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (200 g) with a mixture of chloroform and methanol (50:1) as an eluent

Sources & evidence

ORD record
ord-5a47df5726014329923daab875341450
Source dataset
uspto-grants-1988_02
Patent number
US04725601

Reaction notes

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