Phenylacetonitrile → HCID 22599721, compound

HRID 1759863Notes

Reaction equation

HRID 1759863 reaction equation
[CH3:1][C:2](C)([O-:4])[CH3:3].[K+].[C:7]1([CH2:13][C:14]#[N:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[C:17]1[CH:22]=[C:21]([O:23][CH2:24][C:25]#[C:26][CH3:27])[N:20]=[CH:19][N:18]=1.[Cl-].[NH4+]>O1CCCC1>[C:14]([CH:13]([C:17]1[CH:22]=[C:21]([O:23][CH2:24][C:25]#[C:26][CH3:27])[N:20]=[CH:19][N:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[N:15].[C:2]([C:3]1[CH:22]=[C:21]([O:23][CH2:24][C:25]#[C:26][CH3:27])[N:20]=[CH:19][N:18]=1)(=[O:4])[C:1]1[CH:11]=[CH:12][CH:7]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 8794PhenylacetonitrileHCID 25517Ammonium ChlorideHCID 121376024-(2-Butynyloxy)-6-chloropyrimidineHCID 23665647Potassium tert-butoxide

Product 2

HCID 22599721HCID 22599721, compoundHCID 22599867HCID 22599867, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 5 ml of tetrahydrofuran was suspended 0.46 g of potassium t-butoxide, to which 0.39 g of phenylacetonitrile and 0.5 g of 4-chloro-6-(2-butynyloxy)pyrimidine were added, followed by stirring at room temperature for 8 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The chloroform layers were combined and washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 0.16 g of 4-(a-cyanobenzyl)-6-(2-butynyloxy)pyrimidine (the present compound (74)) and 0.19 g of 4-benzoyl-6-(2-butynyloxy)pyrimidine (the present compound (75)).

Workup

  1. extractionextracted three times with chloroform
  2. washwashed with a saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9dbeb942282e4bd9babf57c6943e4031
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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