Sodium Carbonate → 4-[4-Morpholin-4-yl-6-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1,3,5-triazin-2-yl]aniline

HRID 707077Notes

Reaction equation

HRID 707077 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([N:14]2[CH2:20][CH:19]3[O:21][CH:16]([CH2:17][CH2:18]3)[CH2:15]2)[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH2:28][C:29]1[CH:34]=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][CH:30]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[N:8]1([C:6]2[N:5]=[C:4]([N:14]3[CH2:20][CH:19]4[O:21][CH:16]([CH2:17][CH2:18]4)[CH2:15]3)[N:3]=[C:2]([C:32]3[CH:33]=[CH:34][C:29]([NH2:28])=[CH:30][CH:31]=3)[N:7]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 579982803-(4-Chloro-6-morpholin-4-yl-1,3,5-triazin-2-yl)-8-oxa-3-azabicyclo[3.2.1]octane

Product 1

HCID 670218524-[4-Morpholin-4-yl-6-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1,3,5-triazin-2-yl]anilineYield 59%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3-(4-chloro-6-morpholin-4-yl-1,3,5-triazin-2-yl)-8-oxa-3-azabicyclo[3.2.1]octane (2.0 g, 6.4 mmol), tetrakis(triphenylphosphine)palladium (0) in catalytic amount (100 mg), sodium carbonate solution 2 M (5 mL), 4-aminophenylboronic acid pinacol ester (1.5 g, 6.43 mmoles), DME (200 mL) was refluxed for 24 hours. The solvent was evaporated and the residue was dissolved in methylene chloride and filtered though Celite™. The organic layer was washed with water (200 mL) and dried over magnesium sulfate. It was filtered and the solvent was evaporated. The residue was chromatographed on silica gel column using Ethyl acetate/hexanes (1:1) as an eluent, to give 1.4 g, (59% yield) of the titled product. mp. 154; (M+H) 369.4.

Workup

  1. temperaturewas refluxed for 24 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in methylene chloride
  4. filtrationfiltered though Celite™
  5. washThe organic layer was washed with water (200 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationIt was filtered
  8. customthe solvent was evaporated
  9. customThe residue was chromatographed on silica gel column

Sources & evidence

ORD record
ord-a24ea9f8d1cf43ad9bbd30acddbf4da6
Source dataset
uspto-grants-2015_11
Patent number
US09174963B2

Reaction notes

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