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

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

6synthesis methods

Product Name:6-(6-(trifluoromethyl)pyridin-2-yl)-1,3,5-triazine-2,4(1H,3H)-dione
CAS Number:1446507-38-5
Molecular formula:C9H5F3N4O2
Molecular Weight:258.16

108-19-0 Synthesis

108-19-0
360 suppliers
$14.14/5gm:

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

155377-05-2
129 suppliers
$8.00/100mg

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

1446507-38-5
52 suppliers
$38.00/100mg

Yield: 71%

Reaction Conditions:

Stage #1:BIURET;6-(trifluoromethyl)pyridine-2-carboxylic acid methyl ester in ethanol at 30 - 35;Large scale;
Stage #2: with titanium(IV) tetraethanolate in ethanol at 30 - 35;Large scale;
Stage #3: with sodium ethanolate in ethanol at 55 - 65; for 3 h;Large scale;Temperature;Reagent/catalyst;

Steps:

3 Example 3 Preparation of 6-(6-(trifluoromethyl)pyridin-2-yl)- 1 ,3,5-triazine-2,4(1H,3H)- dione with Ti(OEt)4 as dehydrating agent
100801 Mixture of methyl 6-(trifluoromethyl)picolinate (50g, 244 mmol, 1.0 eq.) and biuret (30.2 g, 293 mmol, 1.20 eq.) in 750 mL EtOH was stirred at 30-35°C for 10-20 mm. Titanium tetraethoxide (Ti(OEt)4, 27.8g, 122 mmol, 0.5 eq.) was added and stirred at 30-35°C for 30-60 mi EtONa solution in EtOH (350 g, 19% wt, 978 mmol, 4.0 eq.) was added, and the reaction mixture was heated at 55-65°C for 3 hours. The reaction mixture was concentrated, cooled to room temperature, and diluted with 700 mL water. Concentrated HC1 solution was added to adjust pH value to pH1. Methylene chloride (DCM, 700 mL) was charged, and the slurry was stirred 20-30°C for 5-7 hours. Solid was collected by filtration, and the cake was sequentially washed twice with 6N HC1, twice with water, and once with DCM. The wet cake was dried at 50-60°C under vacuum, yielding 6-(6-(trifluoromethyl)pyridin-2-yl)- 1,3 ,5-triazine-2,4( 1H,3H)- dione as off-white solid (45.0 g, 174 mmol, 71% yield).

References:

AGIOS PHARMACEUTICALS, INC.;ZHANG, Shijie WO2017/24134, 2017, A1 Location in patent:Paragraph 0073; 0075; 0079; 0080; 0082