Sodium Carbonate → 4-(4,6-Dimorpholino-1,3,5-triazin-2-yl)aniline

HRID 707061Notes

Reaction equation

HRID 707061 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[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH2:26][C:27]1[CH:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][CH:28]=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:14]1([C:4]2[N:5]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[N:7]=[C:2]([C:30]3[CH:31]=[CH:32][C:27]([NH2:26])=[CH:28][CH:29]=3)[N:3]=2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2249672-Chloro-4,6-bis(morpholin-4-yl)-1,3,5-triazineHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 453790874-(4,6-Dimorpholino-1,3,5-triazin-2-yl)anilineYield 83%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-chloro-4,6-di-morpholin-4-yl-[1,3,5]triazine (1.4 g, 4.9 mmoles), a catalytic amount of tetrakis(triphenylphosphine)palladium(0) (70 mg, 0.061 mmoles), sodium carbonate solution 2 M (3 mL), 4-aminophenylboronic acid pinacol ester (1.6 g, 7.3 mmoles) and DME (100 mL) was refluxed for 24 hours. The solvent was evaporated, and the residue was dissolved in methylene chloride and filtered through Celite™. The filtrate was washed with water (200 mL) and the organic layer was dried with magnesium sulfate. This was filtered and the solvent was evaporated. The residue was purified by Silica gel column chromatography and eluted with Ethyl acetate/hexanes (1:1) to give 1.40 g, (83% yield) of 4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)aniline as an amorphous solid. (M+H) 343.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in methylene chloride
  3. filtrationfiltered through Celite™
  4. washThe filtrate was washed with water (200 mL)
  5. dry with materialthe organic layer was dried with magnesium sulfate
  6. filtrationThis was filtered
  7. customthe solvent was evaporated
  8. customThe residue was purified by Silica gel column chromatography
  9. washeluted with Ethyl acetate/hexanes (1:1)

Sources & evidence

ORD record
ord-86a8995e48e14a4798709011a064f9af
Source dataset
uspto-grants-2015_11
Patent number
US09174963B2

Reaction notes

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