4-(2-(6-Chloropyridin-3-ylamino)pyridin-3-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine → 4-(2-(6-Chloropyridin-3-ylamino)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

HRID 1811838Notes

Reaction equation

HRID 1811838 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([C:15]3[N:20]=[C:19]([CH3:21])[N:18]=[C:17]([N:22](CC4C=CC(OC)=CC=4)CC4C=CC(OC)=CC=4)[N:16]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([C:15]3[N:20]=[C:19]([CH3:21])[N:18]=[C:17]([NH2:22])[N:16]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 595482274-(2-(6-Chloropyridin-3-ylamino)pyridin-3-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 595483454-(2-(6-Chloropyridin-3-ylamino)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amineYield 98.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-(2-(6-chloropyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (70 mg, 0.126 mmol) in TFA (10 mL) was heated to 80° C. After 24 h, the mixture was concentrated to a slurry. Water (5 mL) was added, followed by the addition of Na2CO3 in batches until the pH was basic. The mixture was filtered and the solid was washed with water, then MeOH, to give the product as a brown solid (39 mg). LCMS (ES, pos.): calcd for C14H12ClN7: 313.1; found: 314.0 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 12.16 (s, 1H); 8.87 (d, J=2.74 Hz, 1H); 8.82 (dd, J=7.83, 1.76 Hz, 1H); 8.48 (dd, J=8.80, 2.74 Hz, 1H); 8.39 (dd, J=4.50, 1.76 Hz, 1H); 7.92 (br. s., 1H); 7.78 (br. s., 1H); 7.46 (d, J=8.61 Hz, 1H); 7.01 (dd, J=7.83, 4.70 Hz, 1H); 2.44 (s, 3H).

Workup

  1. concentrationthe mixture was concentrated to a slurry
  2. additionWater (5 mL) was added
  3. additionfollowed by the addition of Na2CO3 in batches until the pH
  4. filtrationThe mixture was filtered
  5. washthe solid was washed with water

Sources & evidence

ORD record
ord-c475e7c291374fcda704f1bb1db2ee3e
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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