3-Amino-5-methylpyridine → N,N-Bis(4-methoxybenzyl)-4-methyl-6-(2-(5-methylpyridin-3-ylamino)pyridin-3-YL)-1,3,5-triazin-2-amine

HRID 1812046Notes

Reaction equation

HRID 1812046 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.F[C:10]1[C:15]([C:16]2[N:21]=[C:20]([CH3:22])[N:19]=[C:18]([N:23]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=3)[CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[N:17]=2)=[CH:14][CH:13]=[CH:12][N:11]=1>>[CH3:41][O:40][C:37]1[CH:36]=[CH:35][C:34]([CH2:33][N:23]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[C:18]2[N:19]=[C:20]([CH3:22])[N:21]=[C:16]([C:15]3[C:10]([NH:8][C:4]4[CH:5]=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=4)=[N:11][CH:12]=[CH:13][CH:14]=3)[N:17]=2)=[CH:39][CH:38]=1

Participants

3

Reactant 2

HCID 27628943-Amino-5-methylpyridineHCID 595482404-(2-fluoropyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 66611294N,N-Bis(4-methoxybenzyl)-4-methyl-6-(2-(5-methylpyridin-3-ylamino)pyridin-3-YL)-1,3,5-triazin-2-amineYield 25.7%

Procedure

The title compound was prepared in an analogous manner to that described in Example 164 using 5-methylpyridin-3-amine (0.075 g, 0.690 mmol) (Aldrich) and 4-(2-fluoropyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine. Purification using an ISCO Combiflash Companion (12 g column, 30-70% EtOAc in hexanes over 30 min; the product eluted with 45% EtOAc) gave the title compound as a yellow amorphous solid (25.7%). 1H NMR (400 MHz, d6-DMSO) δ 11.93 (s, 1H); 8.81 (dd, J=7.8, 1.8 Hz, 1H); 8.61 (d, J=2.3 Hz, 1H); 8.39 (dd, J=4.7, 2.0 Hz, 1H); 8.02 (s, 1H); 7.93 (s, 1H); 7.25 (dd, J=10.2, 8.8 Hz, 4H); 6.85-7.00 (m, 5H); 4.82 (d, J=14.7 Hz, 4H); 3.74 (s, 3H); 3.71 (s, 3H); 2.59 (s, 3H); 2.26 (s, 3H). m/z (ESI, +ve ion) 534.0 (M+H)+.

Workup

  1. customThe title compound was prepared in an analogous manner to that
  2. customPurification
  3. customover 30 min
  4. washthe product eluted with 45% EtOAc)

Sources & evidence

ORD record
ord-49d3ceb518fc4e3db51b2762857ada4a
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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