Water → 6-(2,6-Dichlorophenyl)-N2-phenyl-pyrido[2,3-d]-pyrimidine-2,7-diamine

HRID 617959Notes

Reaction equation

HRID 617959 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[CH2:11][C:12]#[N:13].[NH2:14][C:15]1[C:20]([CH:21]=O)=[CH:19][N:18]=[C:17]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:16]=1.O>C(OCCO)C>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[C:11]1[C:12]([NH2:13])=[N:14][C:15]2[N:16]=[C:17]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:18]=[CH:19][C:20]=2[CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 76678(2,6-Dichlorophenyl)acetonitrileHCID 183753114-Amino-2-phenylamino-pyrimidine-5-carboxaldehyde

Product 1

HCID 702851636-(2,6-Dichlorophenyl)-N2-phenyl-pyrido[2,3-d]-pyrimidine-2,7-diamineYield 68.4%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

To a solution of 0.022 g 60% sodium hydride suspension in 2.00 mL of 2-ethoxyethanol was added 0.46 g of 2,6-dichlorophenylacetonitrile and 0.50 g of 4-amino-2-phenylamino-pyrimidine-5-carboxaldehyde from Example 72. The reaction was refluxed for 4 hours, cooled, poured into water, and extracted several times with dichloromethane. The dichloromethane washes were combined, washed with saturated sodium chloride, dried with magnesium sulfate, and concentrated in vacuo. The residue was washed with diethyl ether to give 0.61 g of the title compound, CIMS (1% NH3 in CH4): 410=M+ +C2H5, 382=M+ +H, 381=M+.

Workup

  1. temperatureThe reaction was refluxed for 4 hours
  2. temperaturecooled
  3. extractionextracted several times with dichloromethane
  4. washwashed with saturated sodium chloride
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-f846fad7421d48f8af11cbadf2235352
Source dataset
uspto-grants-1999_09
Patent number
US05952342

Reaction notes

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