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

HRID 404405

반응식

HRID 404405 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d40cb0d8227f4eef82b113806fed0bab
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748421B2

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