HCID 66599854, compound → 4-(2-(6-methoxypyridin-3-ylamino)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

HRID 1621755Notes

Reaction equation

COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[C:13]([C:15]3[C:16]([NH:27][C:28]4[CH:29]=[N:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=4)=[N:17][CH:18]=[C:19]([C:21]4[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=4)[CH:20]=3)[N:12]=[C:11]([CH3:36])[N:10]=2)=CC=1>C(O)(C(F)(F)F)=O>[CH3:35][O:34][C:31]1[N:30]=[CH:29][C:28]([NH:27][C:16]2[C:15]([C:13]3[N:12]=[C:11]([CH3:36])[N:10]=[C:9]([NH2:8])[N:14]=3)=[CH:20][C:19]([C:21]3[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=3)=[CH:18][N:17]=2)=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 80 °C

Procedure

N,N-bis(4-Methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (140 mg, 0.222 mmol) was treated with TFA (10 mL) and heated at 80° C. with a reflux condenser for 18 h. The TFA was removed in vacuo and the residue was treated with 2 M NH3 in MeOH to pH 7 and dry-packed with silica gel. Purification on the ISCO (12 g column, 1-20% MeOH in DCM) gave 4-(2-(6-methoxypyridin-3-ylamino)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (71.7 mg, 0.184 mmol, 83% yield) as an orange crystalline solid. m/z (ESI, +ve ion) 390.0 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 11.69 (1H, s); 8.87 (1H, d, J=2.5 Hz); 8.55 (2H, t, J=3.1 Hz); 8.18 (1H, dd, J=8.8, 2.7 Hz); 8.12 (1H, s); 7.90 (1H, s); 7.82 (1H, s); 7.77 (1H, s); 6.84 (1H, d, J=8.8 Hz); 3.88 (3H, s); 3.85 (3H, s); 2.46 (3H, s).

Workup

customThe TFA was removed in vacuo
additionthe residue was treated with 2 M NH3 in MeOH to pH 7 and dry-packed with silica gel
customPurification on the ISCO (12 g column, 1-20% MeOH in DCM)

Sources & evidence

ORD record: ord-c5eb6a0549eb40bc9d9c1029acc554a3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772480B2

Reaction notes

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