1,2-Dimethoxyethane → 4-(2-Chloroquinolin-3-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

HRID 1621741Notes

Reaction equation

HRID 1621741 reaction equation
I[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:3]=1.[Cl:28][C:29]1[C:38](B(O)O)=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:30]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[Cl:28][C:29]1[C:38]([C:2]2[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[N:3]=2)=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:30]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 41986432-Chloroquinoline-3-boronic acidHCID 601556234-iodo-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 866470604-(2-Chloroquinolin-3-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A 10 mL reaction vial was charged with 4-iodo-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.36 g, 0.75 mmol, Example 115), 2-chloroquinolin-3-ylboronic acid (0.31 g, 1.50 mmol, Aldrich, St. Louis, Mo.), sodium carbonate (0.16 g, 1.50 mmol), tetrakis(triphenylphosphine)palladium (0) (43 mg, 0.04 mmol, Strem, Newburyport, Mass.), DME (4 mL), and water (1 mL). The vial was sealed and purged with argon for several minutes. The reaction mixture was stirred at 90° C. for 5 h and then allowed to cool to room. The organic phase was taken and the solvents removed under vacuum. The crude material was adsorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g) eluting with a gradient of 0% to 1% 2 M NH3.MeOH in CH2Cl2. The title compound was obtained as a yellow solid (90% pure) and used without further purification. m/z (ESI, +ve ion) 511.8 (M+H)+.

Workup

  1. customA 10 mL reaction
  2. customThe vial was sealed
  3. custompurged with argon for several minutes
  4. temperatureto cool to room
  5. customthe solvents removed under vacuum
  6. custompurified by chromatography through a Redi-Sep pre-packed silica gel column (12 g)
  7. washeluting with a gradient of 0% to 1% 2 M NH3

Sources & evidence

ORD record
ord-14acc6bd226e4193af25ea13fc3f5ad0
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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