Potassium Carbonate → 6-(3,5-Dimethoxy-phenyl)-8-ethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylideneamine

HRID 1793878Notes

Reaction equation

HRID 1793878 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([CH:10]=O)=[CH:8][N:7]=[C:6]([S:12][CH3:13])[N:5]=1)[CH3:2].CO[C:16]1[CH:17]=[C:18]([CH2:24][C:25]#[N:26])[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1.[C:27]([O-:30])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:23][O:22][C:20]1[CH:19]=[C:18]([C:24]2[C:25](=[NH:26])[N:3]([CH2:1][CH3:2])[C:4]3[N:5]=[C:6]([S:12][CH3:13])[N:7]=[CH:8][C:9]=3[CH:10]=2)[CH:17]=[C:16]([O:30][CH3:27])[CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1394453,5-DimethoxyphenylacetonitrileHCID 107504444-(Ethylamino)-2-(methylthio)pyrimidine-5-carbaldehyde2×

Product 1

HCID 222201776-(3,5-Dimethoxy-phenyl)-8-ethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylideneamineYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of Example 3, 4-ethylamino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde (37.0 g, 0.19 mol) and 3,5-dimethoxyphenylacetonitrile (37.0 g, 0.21 mol) in DMF (300 mL) was added portionwise anhydrous K2CO3 (130 g) with stirring. The reaction mixture was heated overnight at 105–110° C. and filtered hot. The insoluble salts were washed with DMF (100 mL), and water was added to the warm filtrate until the solution just turned turbid. Crystals developed upon seeding or inducement (scratching with a glass rod). The product was collected by filtration, washed with 100 mL DMF/H2O (25:75), washed with water, and dried in vacuo to afford 50.5 g (76%) of the titled compound. mp 93–95° C.

Workup

  1. temperatureThe reaction mixture was heated overnight at 105–110° C.
  2. filtrationfiltered hot
  3. washThe insoluble salts were washed with DMF (100 mL), and water
  4. additionwas added to the warm filtrate until the solution just turned turbid
  5. filtrationThe product was collected by filtration
  6. washwashed with 100 mL DMF/H2O (25:75)
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-b253223e501e42c8b794043a5caa9902
Source dataset
uspto-grants-2006_04
Patent number
US07022711B2

Reaction notes

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