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

HRID 1812047Notes

Reaction equation

HRID 1812047 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[C:17]([NH:22][C:23]4[CH:24]=[N:25][CH:26]=[C:27]([CH3:29])[CH:28]=4)=[N:18][CH:19]=[CH:20][CH:21]=3)[N:10]=2)=CC=1>C(O)(C(F)(F)F)=O>[CH3:15][C:13]1[N:12]=[C:11]([C:16]2[C:17]([NH:22][C:23]3[CH:24]=[N:25][CH:26]=[C:27]([CH3:29])[CH:28]=3)=[N:18][CH:19]=[CH:20][CH:21]=2)[N:10]=[C:9]([NH2:8])[N:14]=1

Participants

3

Reactant 1

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

Product 1

HCID 595484134-Methyl-6-(2-(5-methylpyridin-3-ylamino)pyridin-3-yl)-1,3,5-triazin-2-amineYield 39.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N,N-bis(4-methoxybenzyl)-4-methyl-6-(2-(5-methylpyridin-3-ylamino)pyridin-3-yl)-1,3,5-triazin-2-amine (0.063 g, 0.118 mmol) in TFA (3.0 mL) (Aldrich) was heated at 80° C. overnight. The solution was cooled to room temperature and was concentrated to about 50% of the original volume. The remaining mixture was pipetted carefully into a saturated solution of NaHCO3, which had been cooled in an ice bath. The resulting precipitate was removed by filtration and washed with water. The material was suspended in DMSO (5mL) and water (10 drops) was added. The solid was collected by filtration to give 4-methyl-6-(2-(5-methylpyridin-3-ylamino)pyridin-3-yl)-1,3,5-triazin-2-amine (0.0137 g, 0.047 mmol, 39.6% yield) as a yellow amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 11.96-12.04 (m, 1H); 8.81 (br. s., 2H); 8.39 (br. s., 1H); 8.23 (br. s., 1H); 8.05 (s, 1H); 7.89 (br. s., 1H); 7.77 (br. s., 1H); 6.96 (br. s., 1H); 2.45 (br. s., 3H); 2.32 (s, 3H). m/z (ESI, +ve ion) 294.0 (M+H)+.

Workup

  1. concentrationwas concentrated to about 50% of the original volume
  2. temperaturehad been cooled in an ice bath
  3. customThe resulting precipitate was removed by filtration
  4. washwashed with water
  5. additionwater (10 drops) was added
  6. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-91698414c9be4565a5bf591fe0759bf8
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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