Sodium hydride → 6-(2,6-Dibromophenyl)pyrido[2,3-d]pyrimidine-2,7-diamine

HRID 3444

Reaction equation

HRID 3444 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:5]=1[CH2:11][C:12]#[N:13].[NH2:14][C:15]1[N:20]=[C:19]([NH2:21])[C:18]([CH:22]=O)=[CH:17][N:16]=1>C(OCCO)C>[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:5]=1[C:11]1[C:12]([NH2:13])=[N:21][C:19]2[N:20]=[C:15]([NH2:14])[N:16]=[CH:17][C:18]=2[CH:22]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3091762,4-Diaminopyrimidine-5-carbaldehydeHCID 218500422-(2,6-Dibromophenyl)acetonitrile

Product 1

HCID 53281206-(2,6-Dibromophenyl)pyrido[2,3-d]pyrimidine-2,7-diamineYield 63.3%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

To a solution of 0.23 g 60% sodium hydride suspension in 11.0 mL of 2-ethoxyethanol was added 4.18 g of 2,6-dibromophenylacetonitrile and 2.00 g of 2,4-diaminopyrimidine-5-carboxaldehyde. The reaction was refluxed for 4 hours, cooled, and poured into ice water. The residue was washed well with acetonitrile then diethyl ether to give 3.62 g of 6-(2,6-dibromo-phenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine, CIMS (1% NH3 in CH4): 422=M+ +C2H5, 396 (Base), 394=M+ +H, 393=M+ ; mp 284°-289° C.

Workup

  1. temperatureThe reaction was refluxed for 4 hours
  2. temperaturecooled
  3. washThe residue was washed well with acetonitrile

Sources & evidence

ORD record
ord-c9858bf611994d008d92d1a95facaa9c
Source dataset
uspto-grants-1998_03
Patent number
US05733913

Linked notes

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