Sodium Carbonate → 4-{4-[(3s)-3-Methylmorpholin-4-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl}aniline

HRID 404454

反応式

HRID 404454 の反応式
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[CH3:14])[N:5]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH2:27][C:28]1[CH:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][CH:29]=1>COCCOC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].[Pd].[Pd].[Pd]>[CH3:14][C@H:9]1[CH2:10][O:11][CH2:12][CH2:13][N:8]1[C:6]1[N:5]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=[C:2]([C:31]2[CH:32]=[CH:33][C:28]([NH2:27])=[CH:29][CH:30]=2)[N:7]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 872396542-Chloro-4-[(35)-3-methylmorpholin-4-yl]-6-morpholin-4-yl-1,3,5-triazine

生成物 1

HCID 670219084-{4-[(3s)-3-Methylmorpholin-4-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl}aniline収率 71%

試薬・触媒・溶媒 2

HCID 86600928Tetrakis palladium triphenylphosphine触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of 2-chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-morpholin-4-yl-1,3,5-triazine (1.26, 4.2 mmol), sodium carbonate solution (2M, 2 mL), tetrakis palladium triphenylphosphine 70 mg (catalytic amount) and 4-aminophenyl boronic pinacol ester (1.37 g, 6.3 mmoles) in DME (100 mL) was heated to reflux for 24 hours. The solvent was evaporated, the residue was re-dissolved in methylene chloride and filtered through Celite™. The solvent was evaporated and the residue was chromatographed on silica gel eluting with first 26/4 hexanes/ethyl acetate then increased to 1/1 hexanes ethyl acetate to give 1.0 of 4-{4-[(3S)-3-methylmorpholin-4-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl}aniline (71% yield); M+H 357.2.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. customThe solvent was evaporated
  4. dissolutionthe residue was re-dissolved in methylene chloride
  5. filtrationfiltered through Celite™
  6. customThe solvent was evaporated
  7. customthe residue was chromatographed on silica gel eluting with first 26/4 hexanes/ethyl acetate
  8. temperaturethen increased to 1/1 hexanes ethyl acetate

出典と根拠

ORDレコード
ord-9b74d0fa922946cc822f8abf15ce1935
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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