Water → Tert-butyl 2-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-YL)-6-fluoropyridin-3-YL)acetate

HRID 1621980

反応式

HRID 1621980 の反応式
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:3]=1.[F:28][C:29]1[N:34]=[CH:33][C:32]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:31][C:30]=1B1OC(=O)CN(C)CC(=O)O1.C(=O)([O-])[O-].[K+].[K+].O>CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl.O1CCOCC1>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:4]2[N:5]=[C:6]([CH3:8])[N:7]=[C:2]([C:30]3[CH:31]=[C:32]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH:33]=[N:34][C:29]=3[F:28])[N:3]=2)=[CH:12][CH:13]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 595482094-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amineHCID 66612120HCID 66612120、化合物

生成物 1

HCID 66611512Tert-butyl 2-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-YL)-6-fluoropyridin-3-YL)acetate収率 37%

試薬・触媒・溶媒 2

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

To 4-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.783 g, 2.035 mmol) (Example 51), tert-butyl 2-(6-fluoro-5-(6-methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)pyridin-3-yl)acetate (1.49 g, 4.07 mmol), and bis-(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.072 g, 0.102 mmol) was added dioxane (20 mL) and potassium carbonate in water (3.05 mL, 6.10 mmol), and the resulting mixture was heated at 80° C. for 1 h. The reaction mixture was then added to a separatory funnel and partitioned between EtOAc (100 mL) and sodium bicarbonate (saturated, aqueous). The organic layer was separated, washed 2 times with 75 mL of sodium bicarbonate (saturated, aqueous), dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel; 0% to 40% EtOAc/hexanes) gave the title compound (37% yield). m/z (ESI, +ve ion) 560.4 (M+H)+.

後処理

  1. additionThe reaction mixture was then added to a separatory funnel
  2. custompartitioned between EtOAc (100 mL) and sodium bicarbonate (saturated, aqueous)
  3. customThe organic layer was separated
  4. washwashed 2 times with 75 mL of sodium bicarbonate (saturated, aqueous)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customChromatographic purification of the residue (silica gel; 0% to 40% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-80a6ad783deb40588163de600bb65eb2
出典データセット
uspto-grants-2014_07
特許番号
US08772480B2

関連ノート

読み込み中…