Triethylamine → 4-[2-(2-fluoroethoxy)-6-[2-(trimethylsilyl)ethynyl]-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine

HRID 1398688노트

반응식

HRID 1398688 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([O:10][CH2:11][CH2:12][F:13])[N:7]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=3)[C:6]=2[CH:21]=1.[C:22]([Si:24]([CH3:27])([CH3:26])[CH3:25])#[CH:23].C(N(CC)CC)C>CS(C)=O.ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:13][CH2:12][CH2:11][O:10][C:8]1[N:7]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=2)[C:6]2[CH:21]=[C:2]([C:23]#[C:22][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:3]=[CH:4][C:5]=2[N:9]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 866696134-[6-bromo-2-(2-fluoroethoxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine

생성물 1

HCID 866696144-[2-(2-fluoroethoxy)-6-[2-(trimethylsilyl)ethynyl]-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine수율 38%

시약·촉매·용매 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매

실험 절차

A solution of 4-[6-bromo-2-(2-fluoroethoxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (150 mg, 0.43 mmol), ethynyltrimethylsilane (126 mg, 1.28 mmol), bis(triphenylphosphine) palladium(II) dichloride (120 mg, 0.17 mmol) and triethylamine (0.5 mL) in dimethylsulfoxide (1 mL) was irradiated with microwave radiation under nitrogen in a sealed tube at 80° C. for 40 min. The reaction mixture was diluted with 10 mL of dichloromethane and the solid material was removed by filtration. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column (ethyl acetate/petroleum ether, 3:1) to give 60 mg (38%) of 4-[2-(2-fluoroethoxy)-6-[2-(trimethylsilyl)ethynyl]-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine as a yellow solid: LC-MS: m/z=+370 (M+H)+.

후처리

  1. customthe solid material was removed by filtration
  2. concentrationThe filtrate was concentrated under vacuum
  3. customthe residue was purified on a silica gel column (ethyl acetate/petroleum ether, 3:1)

출처 및 근거

ORD 기록
ord-642ebf2a509d47148e8dbb6daac94ec7
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901313B2

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