Sodium Carbonate → 2-(4-Penten-1-yl)-4-phenylpyrimidine

HRID 19662

Reaction equation

HRID 19662 reaction equation
Cl.[C:2](=[NH:9])([NH2:8])[CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].[C:10]1([C:16]#[C:17][CH:18]=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH2:3]([C:2]1[N:8]=[C:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:17]=[CH:18][N:9]=1)[CH2:4][CH2:5][CH:6]=[CH2:7]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 75740PhenylpropynalHCID 552849605-Hexenimidamide hydrochloride

Product 1

HCID 578564872-(4-Penten-1-yl)-4-phenylpyrimidineYield 20.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-hexenimidamide hydrochloride (P4, 500 mg), 3-phenyl-2-propynal (398 mg), and sodium carbonate (786 mg) in acetonitrile (15 mL) was irradiated in a microwave synthesizer at 120° C. for 40 min and then allowed to cool. The solution was filtered and evaporated in vacuo. The residue was dissolved in dichloromethane and the organic layer was washed with H2O, dried over Na2SO4, filtered and evaporated in vacuo. The crude was purified by column chromatography (eluting with ciclohexane/ethyl acetate 9/1) to give 142 mg of the title compound.

Workup

  1. customwas irradiated in a microwave synthesizer at 120° C. for 40 min
  2. temperatureto cool
  3. filtrationThe solution was filtered
  4. customevaporated in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washthe organic layer was washed with H2O
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe crude was purified by column chromatography (eluting with ciclohexane/ethyl acetate 9/1)

Sources & evidence

ORD record
ord-f462b44746bc4591972fdb750e1a415d
Source dataset
uspto-grants-2010_06
Patent number
US07745458B2

Linked notes

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