Trifluoromethanesulfonic acid → 4-(5-Chloro-2-fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([N:16](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[N:10]=2)[C:5]([F:8])=[N:6][CH:7]=1.FC(F)(F)S(O)(=O)=O>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH2:16])[N:10]=2)[C:5]([F:8])=[N:6][CH:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
4-(5-Chloro-2-fluoropyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (3.87 g, 8.06 mmol) (Example 313, Step 1) was dissolved in TFA (81 mL), trifluoromethanesulfonic acid (2.1 mL, 24 mmol) was added, and the resulting mixture was stirred at 80° C. for 2 h. The reaction mixture was then concentrated in vacuo. The residue was partitioned between EtOAc (150 mL) and sodium bicarbonate (saturated, aqueous). The organic layer was the separated, washed 2 times with 100 mL of sodium bicarbonate (saturated, aqueous), dried over sodium sulfate, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0% to 40% EtOAc/hexanes) provided the title compound (51% yield). m/z (ESI, +ve ion) 240.1 (M+H)+.
Workup
- concentrationThe reaction mixture was then concentrated in vacuo
- customThe residue was partitioned between EtOAc (150 mL) and sodium bicarbonate (saturated, aqueous)
- washwashed 2 times with 100 mL of sodium bicarbonate (saturated, aqueous)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customChromatographic purification of the residue (silica gel, 0% to 40% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-b4bfb81753ea4735b7984ec1cf7a7531
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772480B2
Reaction notes
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