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1446507-38-5

1446507-38-5 Structure

1446507-38-5 Structure
IdentificationBack Directory
[Name]

6-(6-(trifluoromethyl)pyridin-2-yl)-1,3,5-triazine-2,4(1H,3H)-dione
[CAS]

1446507-38-5
[Synonyms]

Enasidenib Intermediate 2
6-(6-(trifluoromethyl)pyridin-2-yl)-1,3,5-triazine-2,4(1H,3H)-dione
1,3,5-Triazine-2,4(1H,3H)-dione, 6-[6-(trifluoromethyl)-2-pyridinyl]-
[Molecular Formula]

C9H5F3N4O2
[MDL Number]

MFCD29044888
[MOL File]

1446507-38-5.mol
[Molecular Weight]

258.16
Chemical PropertiesBack Directory
[density ]

1.74±0.1 g/cm3(Predicted)
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[pka]

4.09±0.70(Predicted)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Synthesis]

Biuret

108-19-0

6-Trifluoromethyl-pyridine-2-carboxylic acid methyl ester

155377-05-2

6-(6-(trifluoromethyl)pyridin-2-yl)-1,3,5-triazine-2,4(1H,3H)-dione

1446507-38-5

1. Methyl 6-(trifluoromethyl)pyridinecarboxylate (50 g, 244 mmol, 1.0 eq.) and urea condensate (30.2 g, 293 mmol, 1.20 eq.) were dissolved in 750 mL of ethanol and stirred for 10-20 min at 30-35 °C. 2. titanium tetraethoxide (Ti(OEt)4, 27.8 g, 122 mmol, 0.5 eq.) was added to the reaction mixture and stirring was continued at 30-35 °C. 3. 350 g of an ethanol solution of 19% wt sodium ethanol (978 mmol, 4.0 eq.) was added slowly and dropwise, then the reaction mixture was heated to 55-65 °C and maintained for 3 hours. 4. Upon completion of the reaction, the reaction mixture was concentrated, cooled to room temperature and diluted with 700 mL of water. 5. pH was adjusted to 1 with concentrated hydrochloric acid solution, 700 mL of dichloromethane (DCM) was added, and the slurry was stirred at 20-30 °C for 5-7 hours. 6. Collect the solid by filtration and wash it sequentially with 6N hydrochloric acid twice, water twice and DCM once. 7. The wet filter cake was dried under vacuum at 50-60 °C to afford 6-(6-(trifluoromethyl)pyridin-2-yl)-1,3,5-triazine-2,4(1H,3H)-dione as a white solid (45.0 g, 174 mmol, 71% yield).

[References]

[1] Patent: WO2017/24134, 2017, A1. Location in patent: Paragraph 0073; 0075; 0079; 0080; 0082
[2] Patent: EP3330258, 2018, A1. Location in patent: Paragraph 0079-0080
[3] Patent: US2015/18328, 2015, A1. Location in patent: Paragraph 0722-0723
[4] Patent: WO2015/3640, 2015, A1. Location in patent: Page/Page column 156; 157
[5] Patent: WO2015/18060, 2015, A1. Location in patent: Page/Page column 48-49
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