Sodium Carbonate Decahydrate → 3-(4-(Cyclohexyloxy)phenyl)-5-methylpyrazin-2-amine

HRID 1622773노트

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HRID 1622773 반응식
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([CH3:8])[N:7]=1.[CH:10]1([O:16][C:17]2[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.O.O.O.O.O.O.O.O.O.O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.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>[CH:17]1([O:16][C:10]2[CH:15]=[CH:14][C:13]([C:2]3[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([CH3:8])[N:7]=3)=[CH:12][CH:11]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

참가 물질

7

반응물 3

HCID 151402Sodium Carbonate DecahydrateHCID 98990432-Amino-3-bromo-5-methylpyrazineHCID 222898184-Cyclohexyloxy-benzeneboronic acid

생성물 1

HCID 667484133-(4-(Cyclohexyloxy)phenyl)-5-methylpyrazin-2-amine수율 99.5%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

Tetrakis(triphenylphosphine)palladium(0) (0.922 g) was added to a suspension of 3-bromo-5-methylpyrazin-2-amine (5 g), 4-(cyclohexyloxy)phenylboronic acid (7.61 g) and sodium carbonate decahydrate (15.2 g) in DME (200 mL) and water (40 mL) and the mixture was stirred at 80° C. under nitrogen overnight. The insoluble material was removed by filtration (eluted with EtOAc), and silica-gel was added and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (7.5 g) as a pale orange solid.

후처리

  1. customThe insoluble material was removed by filtration (eluted with EtOAc), and silica-gel
  2. additionwas added
  3. customthe volatiles were removed in vacuo
  4. customwas purified by column chromatography (silica gel, eluted with EtOAc in hexane)

출처 및 근거

ORD 기록
ord-ff81785239c5466f96cb90ed0191d21a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778934B2

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