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

HRID 1398688ノート

反応式

HRID 1398688 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-642ebf2a509d47148e8dbb6daac94ec7
出典データセット
uspto-grants-2014_12
特許番号
US08901313B2

反応ノート

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