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

HRID 404405

反応式

HRID 404405 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d40cb0d8227f4eef82b113806fed0bab
出典データセット
uspto-grants-2014_06
特許番号
US08748421B2

関連ノート

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