4-(5-(2-azidopropan-2-yl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine → HCID 66610862, compound

HRID 1621817Notes

Reaction equation

HRID 1621817 reaction equation
[N:1]([C:4]([C:7]1[CH:8]=[C:9]([C:22]2[N:27]=[C:26]([CH3:28])[N:25]=[C:24]([N:29]([CH2:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)[CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)[N:23]=2)[C:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[N:11][CH:12]=1)([CH3:6])[CH3:5])=[N+]=[N-]>[Pd]>[NH2:1][C:4]([C:7]1[CH:8]=[C:9]([C:22]2[N:27]=[C:26]([CH3:28])[N:25]=[C:24]([N:29]([CH2:30][C:31]3[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=3)[CH2:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)[N:23]=2)[C:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[N:11][CH:12]=1)([CH3:5])[CH3:6]

Participants

3

Reactant 1

HCID 866470644-(5-(2-azidopropan-2-yl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 66610862HCID 66610862, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-(5-(2-Azidopropan-2-yl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.184 g, 0.291 mmol) and 10% palladium on carbon (0.186 g, 0.174 mmol) were combined in a flask and flushed with nitrogen. THF (5 mL) was added and the reaction was stirred under a H2 atmosphere for 1.5 h. The reaction was filtered through Celite® (diatomaceous earth) rinsing with DCM, and the filtrate was concentrated in vacuo to give 4-(5-(2-aminopropan-2-yl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.176 g, 0.290 mmol, 100% yield). m/z (ESI, +ve ion) 607 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 11.55 (s, 1H); 8.92 (d, J=2.7 Hz, 1H); 8.48 (d, J=2.5 Hz, 1H); 8.23 (d, J=2.5 Hz, 2H); 7.91 (dd, J=8.8, 2.7 Hz, 1H); 7.15-7.25 (m, 4H); 6.78-6.95 (m, 4H); 6.69 (d, J=8.8 Hz, 1H); 4.89 (s, 2H); 4.81 (s, 2H); 3.92 (s, 3H); 3.81 (s, 3H); 3.77 (s, 3H); 2.58 (s, 3H); 1.53 (s, 6H).

Workup

  1. customflushed with nitrogen
  2. additionTHF (5 mL) was added
  3. filtrationThe reaction was filtered through Celite® (diatomaceous earth)
  4. washrinsing with DCM
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-82af8d6f9db64c7485d4f326e6cb0831
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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