(2,6-Dichlorophenyl)acetonitrile → HCID 12904727, compound

HRID 1679890Notes

Reaction equation

HRID 1679890 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]#[N:11].[NH2:12][C:13]1[C:18]([CH:19]=O)=[CH:17][N:16]=[C:15]([CH3:21])[N:14]=1.[Na]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:10]([NH2:11])=[N:12][C:13]2[N:14]=[C:15]([CH3:21])[N:16]=[CH:17][C:18]=2[CH:19]=1

Participants

5

Reactant 3

HCID 76678(2,6-Dichlorophenyl)acetonitrileHCID 5360545SodiumHCID 129047264-Amino-2-methylpyrimidine-5-carbaldehyde

Product 1

HCID 12904727HCID 12904727, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,6-Dichlorophenylacetonitrile 8.1 g and 4-amino-2-methylpyrimidine-5-carboxaldehyde 6.9 g is added to a solution of 0.4 g of sodium metal in 60 ml of anhydrous ethanol. This mixture is heated at reflux for 3 hours. Upon cooling, the crude product precipitates and is collected by filtration. The solid is recrystallized from ethanol, with charcoal treatment, to give 5.5 g of 6-(2,6-dichlorophenyl)-2-methylpyrido[2,3-d]pyrimidin-7-amine, mp 287°-289° C., which may occlude varying amounts of water, depending on the drying conditions.

Workup

  1. temperatureThis mixture is heated
  2. temperatureat reflux for 3 hours
  3. temperatureUpon cooling
  4. customthe crude product precipitates
  5. filtrationis collected by filtration
  6. customThe solid is recrystallized from ethanol, with charcoal treatment

Sources & evidence

ORD record
ord-944daf5a83e9414b9fa4f422811dcd6d
Source dataset
uspto-grants-1981_06
Patent number
US04271164

Reaction notes

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