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

HRID 1621663Notes

Reaction equation

HRID 1621663 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:17]2[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([N:24](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[N:18]=2)[C:5]([NH:8][C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)=[N:6][CH:7]=1>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:17]2[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH2:24])[N:18]=2)[C:5]([NH:8][C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)=[N:6][CH:7]=1

Participants

3

Reactant 1

HCID 666119674-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 595484604-(5-Chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amineYield 100.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (110 mg, 0.188 mmol) in TFA (10 mL) was heated at 80° C. for 16 h. The orange mixture was concentrated to a slurry, diluted with saturated NaHCO3 (5 mL), and filtered. The solid was washed with water, MeOH, and (3:1) hexane-EtOAc to give the product as a brown solid (65 mg). LCMS (ES, pos.): calcd for C15H14ClN7O: 343.1. found: 344.1 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 11.69 (br. s., 1H); 8.72 (br. s., 1H); 8.50 (d, J=3.33 Hz, 1H); 8.31 (br. s., 1H); 8.09 (br. s., 1H); 7.94 (br. s., 1H); 7.80 (br. s., 1H); 6.84 (br. s., 2H); 3.85 (br. s., 3H); 2.43 (br. s., 3H).

Workup

  1. concentrationThe orange mixture was concentrated to a slurry
  2. additiondiluted with saturated NaHCO3 (5 mL)
  3. filtrationfiltered
  4. washThe solid was washed with water, MeOH, and (3:1) hexane-EtOAc

Sources & evidence

ORD record
ord-05b2a09c132844d48c4ef461e333141f
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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