1,2-Dimethoxyethane → HCID 60155703, compound

HRID 1812151Notes

Reaction equation

HRID 1812151 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[NH2:11])O1.Cl[C:18]1[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([N:25]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[N:19]=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>[NH2:11][C:10]1[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=1[C:18]1[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([N:25]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)[CH2:35][C:36]2[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=2)[N:19]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27346522-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 595482094-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 60155703HCID 60155703, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A 20 mL reaction vial was charged with 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.31 g, 1.42 mmol, Oakwood Products, West Columbia, S.C.), tetrakis(triphenylphosphine)palladium (0) (63 mg, 0.06 mmol, Newburyport, Mass.), 4-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.42 g, 1.10 mmol), sodium carbonate (0.29 g, 2.73 mmol), DME (5 mL), and water (1.5 mL). The vial was sealed and purged with argon for several minutes. The reaction mixture was stirred at 90° C. for 2 h and allowed to cool to room temperature. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (20 mL). The organic extract was washed with water and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material. The crude material was adsorbed ontodsilica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g) eluting with a gradient of 0% to 1% MeOH in CH2Cl2 to give the title compound as a light yellow oil. m/z (ESI, +ve ion) 441.9 (M+H)+.

Workup

  1. customA 20 mL reaction
  2. customThe vial was sealed
  3. custompurged with argon for several minutes
  4. temperatureto cool to room temperature
  5. additionThe reaction mixture was diluted with water (10 mL)
  6. extractionextracted with EtOAc (20 mL)
  7. extractionThe organic extract
  8. washwas washed with water
  9. dry with materialdried over Na2SO4
  10. filtrationThe solution was filtered
  11. concentrationconcentrated in vacuo
  12. customto give the crude material
  13. custompurified by chromatography through a Redi-Sep pre-packed silica gel column (40 g)
  14. washeluting with a gradient of 0% to 1% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-2c9b757c6b3a4e19b394e881580ba883
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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