Triethylamine → HCID 19349432, compound

HRID 1636820Notes

Reaction equation

HRID 1636820 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-methylpropi ononitrile), (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-6f8b19a878ff43e28f01f15ff602a9f8
Source dataset
uspto-grants-2000_03
Patent number
USRE036617

Reaction notes

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