Potassium Carbonate → HCID 67271871, compound

HRID 1696441Notes

Reaction equation

HRID 1696441 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([CH:9]=O)=[CH:7][N:6]=[C:5]([S:11][CH3:12])[N:4]=1.[N+:13]([C:16]1[CH:17]=[C:18]([CH2:22][C:23]#[N:24])[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][N:2]1[C:3]2[N:4]=[C:5]([S:11][CH3:12])[N:6]=[CH:7][C:8]=2[CH:9]=[C:22]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=2)[C:23]1=[NH:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 121253-NitrophenylacetonitrileHCID 106075204-(Methylamino)-2-(methylthio)pyrimidine-5-carbaldehyde

Product 1

HCID 67271871HCID 67271871, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carbaldehyde (10.0 g, 55 mmol) and (3-nitrophenyl)acetonitrile (10.5 g, 65 mmol) in DMF (150 mL) was added K2CO3 (38 g, 275 mmol) at RT. The mixture was stirred at 100° C. for 18 h. After cooling, the reaction was diluted with DMF (50 mL) and filtered. The filtrate was concentrated to give crude 8-methyl-2-(methylsulfanyl)-6-(3-nitrophenyl)-8H-pyrido[2,3-d]pyrimidin-7-ylideneamine (9.0 g, 50% yield) which was used in the next reaction without further purification.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e6ac646aea9d4f39a862ffb133643c2f
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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