(4-Bromo-phenyl)-[4-chloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2-YL]-amine → 4-(5-Chloro-2-methyl-phenyl)-6-methoxy-[1,3,5]triazin-2-yl-amine

HRID 1591605Notes

Reaction equation

HRID 1591605 reaction equation
BrC1C=CC([NH:8][C:9]2[N:14]=[C:13](Cl)[N:12]=[C:11]([C:16]3[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=3[CH3:23])[N:10]=2)=CC=1.[CH3:24][O-:25].[Na+]>CO>[Cl:22][C:20]1[CH:19]=[CH:18][C:17]([CH3:23])=[C:16]([C:11]2[N:12]=[C:13]([O:25][CH3:24])[N:14]=[C:9]([NH2:8])[N:10]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 10179730(4-Bromo-phenyl)-[4-chloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2-YL]-amineHCID 10942334Sodium Methoxide

Product 1

HCID 1317266574-(5-Chloro-2-methyl-phenyl)-6-methoxy-[1,3,5]triazin-2-yl-amineYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of the title compound of Example 20 (100 mg, 0.25 mmol) in methanol (5 ml) was added a solution of sodium methoxide in methanol (25-30%, 0.5 ml). After stirring for 72 hours, the mixture was concentrated under reduced pressure. The residue was stirred with water (20 ml). The solid was collected by filtration, washed with hexane (5 ml), and dried under reduced pressure to provide the title compound (60 mg, 59% yield). 1H NMR (DMSO-d6) 10.40 (s, 1H), 7.90 (s, 1H), 7.75 (m, 2H), 7.48-7.55 (m, 3H), 7.38 (m, 1H), 3.98 (s, 3H), 2.54 (s, 3H).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. stirringThe residue was stirred with water (20 ml)
  3. filtrationThe solid was collected by filtration
  4. washwashed with hexane (5 ml)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-f7548e055b5847ea964530d212501469
Source dataset
uspto-grants-2007_11
Patent number
US07291616B2

Reaction notes

Loading…