N,N-Bis(4-methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)phenyl)-6-methyl-1,3,5-triazin-2-amine → 4-(2-(6-Methoxypyridin-3-ylamino)phenyl)-6-methyl-1,3,5-triazin-2-amine

HRID 1621746Notes

Reaction equation

COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[NH:21][C:22]3[CH:23]=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)[N:12]=[C:11]([CH3:30])[N:10]=2)=CC=1>C(O)(C(F)(F)F)=O.FC(F)(F)S(O)(=O)=O>[CH3:29][O:28][C:25]1[N:24]=[CH:23][C:22]([NH:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:13]2[N:12]=[C:11]([CH3:30])[N:10]=[C:9]([NH2:8])[N:14]=2)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of N,N-bis(4-methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)phenyl)-6-methyl-1,3,5-triazin-2-amine (0.38 g, 0.70 mmol) in TFA (3 mL) was treated with several drops of trifluoromethane sulfonic acid and heated at 80° C. for 3 h. The solvent was removed in vacuo and the residue was purified by reverse phase preparative HPLC using a Phenomenex Gemini column, 10 micron, C18, 100 Å, 150×30 mm, 0.1% TFA in MeCN/H2O gradient to give 4-(2-(6-methoxypyridin-3-ylamino)phenyl)-6-methyl-1,3,5-triazin-2-amine (47 mg, 0.15 mmol, 22% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 10.92 (s, 1H); 8.44 (dd, J=8.12, 1.66 Hz, 1H); 8.12 (d, J=2.74 Hz, 1H); 7.68 (dd, J=8.80, 2.74 Hz, 2H); 7.53 (br. s., 1H); 7.28 (ddd, J=8.46, 6.99, 1.57 Hz, 1H); 6.88 (dd, J=12.81, 8.51 Hz, 2H); 6.69-6.82 (m, 1H); 3.86 (s, 3H); 2.38 (s, 3H). m/z (ESI, +ve ion) 309.0 (M+H)+.

Workup

customThe solvent was removed in vacuo
customthe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-f44058bf66354d0fa56857f708d54787
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772480B2

Reaction notes

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