Phenylacetonitrile → 4-(alpha-Cyanobenzyl)-6-methylthiopyrimidine

HRID 1592246Notes

Reaction equation

HRID 1592246 reaction equation
CC(C)([O-])C.[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]([S:23][CH3:24])[N:20]=[CH:19][N:18]=1.[Cl-].[NH4+]>O1CCCC1>[C:14]([CH:13]([C:17]1[CH:22]=[C:21]([S:23][CH3:24])[N:20]=[CH:19][N:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[N:15]

Participants

6

Reactant 4

HCID 8794PhenylacetonitrileHCID 25517Ammonium ChlorideHCID 218130774-Chloro-6-(methylsulfanyl)pyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 225998234-(alpha-Cyanobenzyl)-6-methylthiopyrimidineYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In 30 ml of tetrahydrofuran was suspended 5.24 g of potassium t-butoxide, to which 2.63 g of phenylacetonitrile and 3.0 g of 4-chloro-6-methylthiopyrimidine, followed by stirring at 0° C. for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with ethyl acetate. The organic layers were combined and washed with a saturated aqueous sodium chloride solution, and the combined organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 3.67 g of 4-(α-cyanobenzyl)-6-methylthiopyrimidine.

Workup

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

Sources & evidence

ORD record
ord-af8e15cfc0fb414a87c27e5abdca1b04
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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