(o-Chlorophenyl)acetonitrile → HCID 12904728, compound

HRID 1679891Notes

Reaction equation

HRID 1679891 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].[NH2:11][C:12]1[C:17]([CH:18]=O)=[CH:16][N:15]=[C:14]([CH3:20])[N:13]=1.[Na]>C(OCCO)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([NH2:10])=[N:11][C:12]2[N:13]=[C:14]([CH3:20])[N:15]=[CH:16][C:17]=2[CH:18]=1

Participants

5

Reactant 3

HCID 76112(o-Chlorophenyl)acetonitrileHCID 5360545SodiumHCID 129047264-Amino-2-methylpyrimidine-5-carbaldehyde

Product 1

HCID 12904728HCID 12904728, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

2-Chlorophenylacetonitrile 4.0 g and 4-amino-2-methylpyrimidine-5-carboxaldehyde 3.6 g are added to a solution prepared by dissolving 0.2 g of sodium metal in 40 ml of 2-ethoxy-ethanol. The mixture is heated at reflux for 2 hours, and then cooled. The crude product precipitates as a solid and is collected by filtration. After recrystallization from aqueous dimethylformamide, 3.4 g of 6-(2-chlorophenyl)-2-methylpyrido[2,3-d]pyrimidin-7-amine, mp 259°-260° C. is obtained.

Workup

  1. customprepared
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 2 hours
  4. temperaturecooled
  5. customThe crude product precipitates as a solid
  6. filtrationis collected by filtration
  7. customAfter recrystallization from aqueous dimethylformamide, 3.4 g of 6-(2-chlorophenyl)-2-methylpyrido[2,3-d]pyrimidin-7-amine
  8. custommp 259°-260° C. is obtained

Sources & evidence

ORD record
ord-69e7e87e2ccc4f97a04221bdcb3dd3cd
Source dataset
uspto-grants-1981_06
Patent number
US04271164

Reaction notes

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