Hydrochloric Acid → (Pyrimidin-4-yl)acetonitrile

HRID 2264377Notes

Reaction equation

HRID 2264377 reaction equation
[H-].[Na+].[N:3]1[CH:8]=C[CH:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11].ClC1N=C(Cl)C(C)=C[N:14]=1.Cl>CN(C=O)C.O>[N:11]1[CH:10]=[CH:9][C:4]([CH2:5][C:6]#[N:14])=[N:3][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2×HCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 75959Pyridine-2-acetonitrile

Product 1

HCID 14169572(Pyrimidin-4-yl)acetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of NaH (1.3 g, of NaH in a 60% dispersion oil, 32.5 mmol, 4 eq) in anhydrous DMF (10 mL), was added dropwise at room temperature a solution of 2-pyridylacetonitrile (960 mg, 8.12 mmol, 1 eq) in anhydrous DMF (10 mL). The reaction mixture was stirred at room temperature for 1 hour. A solution of 2,4-dichloro-5-methyl-pyrimidine (1.32 g, 8.12 mmo, 1 eq), dissolved in anhydrous DMF (5 ml), was added dropwise at room temperature. The reaction mixture was stirred at room temperature for 14 hours. The mixture is hydrolysed with water (1 mL) and acidified with 1.6 mL of 10M HCl. The solvents were evaporated under vacuum. The residue was extracted with ethyl acetate. The organic layer was dried over MgSO4 and evaporated to dryness. The residue was purified by column chromatography with 50:50 (EtOAc:cHex). The fractions evaporated to give a yellow solid which was dried under vacuum at 40 degrees. The yellow crystalline product 4-pyrimidineacetonitrile, 2-chloro-5-methyl-alpha-2(1H)-pyridinylidene was isolated. (1.7 g, 86%).

Workup

  1. additionwas added dropwise at room temperature
  2. stirringThe reaction mixture was stirred at room temperature for 14 hours
  3. customThe solvents were evaporated under vacuum
  4. extractionThe residue was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated to dryness
  7. customThe residue was purified by column chromatography with 50:50 (EtOAc:cHex)
  8. customThe fractions evaporated
  9. customto give a yellow solid which
  10. customwas dried under vacuum at 40 degrees

Sources & evidence

ORD record
ord-f98ed04360a24bf19126f825ef68888a
Source dataset
uspto-grants-2010_12
Patent number
US07855212B2

Reaction notes

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