Triethylamine → HCID 19349432, compound

HRID 2107782Notes

Reaction equation

HRID 2107782 reaction equation
Cl[CH:2]([C:9]1[CH:10]=[C:11]([C:20]([CH3:24])([CH3:23])[C:21]#[N:22])[CH:12]=[C:13]([C:15]([CH3:19])([CH3:18])[C:16]#[N:17])[CH:14]=1)[C:3]1[CH:4]=[N:5][CH:6]=[N:7][CH:8]=1.C(N(CC)CC)C>[Pd].C(O)C>[N:5]1[CH:4]=[C:3]([CH2:2][C:9]2[CH:10]=[C:11]([C:20]([CH3:24])([CH3:23])[C:21]#[N:22])[CH:12]=[C:13]([C:15]([CH3:18])([CH3:19])[C:16]#[N:17])[CH:14]=2)[CH:8]=[N:7][CH:6]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 19349404HCID 19349404, compound

Product 1

HCID 19349432HCID 19349432, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2,2'-[5-(1-chloro-1-(pyrimidin-5-yl)methyl)-1,3-phenylene]di(2-methylpropiononitrile), (0.55 g), triethylamine (0.25 ml), 5% palladium-on-carbon (0.02 g) and ethanol (10 ml) was stirred under hydrogen at room temperature and atmospheric pressure for 10 minutes and then filtered. The filtrate was diluted with ethyl acetate (25 ml), and the solution washed with aqueous sodium hydrogen carbonate, dried and evaporated to dryness. The residue was purified by flash chromatography using 1% by volume of methanol in dichloromethane as eluant to give 2,2'-[5-(pyrimidin-5-ylmethyl)-1,3-phenylene]di(2-methylpropiononitrile), mp 132°-134°.

Workup

  1. filtrationfiltered
  2. additionThe filtrate was diluted with ethyl acetate (25 ml)
  3. washthe solution washed with aqueous sodium hydrogen carbonate
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6401a24eeb0f4b79a97e632ed2e41431
Source dataset
uspto-grants-1990_06
Patent number
US04935437

Reaction notes

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