Trifluoroacetic acid → 4-(5-Chloro-2-(tetrahydro-2H-pyran-4-ylamino)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:15]2[N:20]=[C:19]([CH3:21])[N:18]=[C:17]([N:22](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[N:16]=2)[C:5]([NH:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O.S(O)(C(F)(F)F)(=O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([C:15]2[N:20]=[C:19]([CH3:21])[N:18]=[C:17]([NH2:22])[N:16]=2)[C:5]([NH:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[N:6][CH:7]=1Participants
Reactant 3
Product 1
Procedure
A solution of 4-(5-chloro-2-(tetrahydro-2H-pyran-4-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (190 mg, 0.339 mmol) in TFA (5000 μL, 64.9 mmol), and TfOH (100 μL, 1.126 mmol) was heated at 80° C. for 3 h. The mixture was concentrated and stirred with saturated NaHCO3 (10 mL) for 30 min. The suspension was filtered and washed with water (2×5 mL). The resulting solid was briefly rinsed with DCM (5 mL) and EtOAc (5 mL) to give the product as a yellow solid (68 mg). LCMS (ES, pos.): calcd for C14H17ClN6O: 320.1. found: 321.2 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 9.61 (d, J=7.24 Hz, 1H); 8.58 (d, J=2.15 Hz, 1H); 8.23 (d, J=2.15 Hz, 1H); 7.68 (d, J=17.41 Hz, 2H); 4.21 (br. s., 1H); 3.88 (d, J=11.54 Hz, 2H); 3.47 (t, J=10.66 Hz, 2H); 2.38 (s, 3H); 1.92 (d., J=11.932H); 1.64 (q, J=9.59 Hz, 2H).
Workup
- concentrationThe mixture was concentrated
- filtrationThe suspension was filtered
- washwashed with water (2×5 mL)
- washThe resulting solid was briefly rinsed with DCM (5 mL) and EtOAc (5 mL)
Sources & evidence
- ORD record
- ord-68d0bc139e1e46198dc0dc161a28bc82
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772480B2
Reaction notes
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