5-Bromo-2-(phenylthio)benzenamine → (5-Bromo-2-phenylsulfanyl-phenyl)-(7-methyl-pyrido[2,3-d]pyrimidin-4-yl)-amine

HRID 607322Notes

Reaction equation

HRID 607322 reaction equation
[C:1]([C:3]1[C:4]([N:10]=[CH:11][N:12](C)C)=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1)#[N:2].[Br:15][C:16]1[CH:17]=[CH:18][C:19]([S:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:20](N)[CH:21]=1>C(O)(=O)C>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([S:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:18]([NH:2][C:1]2[C:3]3[CH:8]=[CH:7][C:6]([CH3:9])=[N:5][C:4]=3[N:10]=[CH:11][N:12]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 284015215-Bromo-2-(phenylthio)benzenamineHCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine

Product 1

HCID 66808590(5-Bromo-2-phenylsulfanyl-phenyl)-(7-methyl-pyrido[2,3-d]pyrimidin-4-yl)-amineYield 65.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of the product from Example 10B (0.188 g, 1.0 mmol) and 5-bromo-2-(phenylthio)benzenamine (0.280 g, 1.0 mmol) in glacial acetic acid (2 mL) was heated in a 130° C. oil bath for 30 min. The reaction mixture was then cooled to room temperature and the solvent evaporated under reduced pressure. The residue was triturated with methanol, and the resulting solid isolated by vacuum filtration and dried to provide the title compound (0.276 g, 65% yield) as a beige solid.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customthe solvent evaporated under reduced pressure
  3. customThe residue was triturated with methanol
  4. customthe resulting solid isolated by vacuum filtration
  5. customdried

Sources & evidence

ORD record
ord-089cc048767843ea935f84d80ee8290a
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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