Water → Tert-butyl (4-{4-[(isopropylsulfonyl)methyl]-6-morpholin-4-ylpyrimidin-2-yl}phenyl)carbamate

HRID 2353662ノート

反応式

HRID 2353662 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)[CH:5]=[C:4]([CH2:14][S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[N:3]=1.O.[C:22]([O:26][C:27]([NH:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C(COC)OC.C(O)C>[CH:18]([S:15]([CH2:14][C:4]1[CH:5]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:7]=[C:2]([C:33]2[CH:32]=[CH:31][C:30]([NH:29][C:27](=[O:28])[O:26][C:22]([CH3:24])([CH3:23])[CH3:25])=[CH:35][CH:34]=2)[N:3]=1)(=[O:17])=[O:16])([CH3:20])[CH3:19]

参加物

8

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 3613184(4-Boc-Aminophenyl)Boronic AcidHCID 593801124-(2-Chloro-6-(isopropylsulfonylmethyl)pyrimidin-4-yl)morpholine

生成物 1

HCID 59380012Tert-butyl (4-{4-[(isopropylsulfonyl)methyl]-6-morpholin-4-ylpyrimidin-2-yl}phenyl)carbamate

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

4-{2-Chloro-6-[(isopropylsulfonyl)methyl]pyrimidin-4-yl}morpholine (1.5 g, 4.69 mmol) was dissolved in a solution of 18% DMF in a mixture of 7:3:2 dimethoxyethane:water:ethanol (36 mL). {4-[(Tert-butoxycarbonyl)amino]phenyl}boronic acid (1.67 g, 7.04 mmol), 2M sodium carbonate solution (12 mL) and dichlorobis(triphenylphosphine) palladium catalyst (165 mg, 0.23 mmol) were then added and the reaction refluxed at 90° C. for 2 hours under a nitrogen atmosphere. The reaction was allowed to cool to room temp then partitioned between ethyl acetate (20 mL) and water (20 mL). The organics were dried over magnesium sulphate, filtered and concentrated in vacuo. The crude oil was dissolved in DCM and filtered to remove insoluble material. A brown solid precipitated from the filtrates and the filtrates were filtered again. The solid was analysed and found to be the desired material (1.9 g).

後処理

  1. temperatureto cool to room temp
  2. customthen partitioned between ethyl acetate (20 mL) and water (20 mL)
  3. dry with materialThe organics were dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude oil was dissolved in DCM
  7. filtrationfiltered
  8. customto remove insoluble material
  9. customA brown solid precipitated from the filtrates
  10. filtrationthe filtrates were filtered again

出典と根拠

ORDレコード
ord-de9bdd23f0d9435cb597d03518986758
出典データセット
uspto-grants-2010_07
特許番号
US07750003B2

反応ノート

読み込み中…