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

HRID 2353662노트

반응식

HRID 2353662 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 6228Dimethylformamide용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-de9bdd23f0d9435cb597d03518986758
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07750003B2

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