2-(Methylthio)-4-(tributylstannyl)pyrimidine → Methyl-[3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-carbamic acid tert-butyl ester

HRID 1186464

反応式

HRID 1186464 の反応式
[CH3:1][S:2][C:3]1[N:8]=[C:7]([Sn](CCCC)(CCCC)CCCC)[CH:6]=[CH:5][N:4]=1.[C:22]([O:26][C:27](=[O:40])[N:28]([C:30]1[C:31]2[N:32]([C:36](Br)=[CH:37][N:38]=2)[CH:33]=[CH:34][N:35]=1)[CH3:29])([CH3:25])([CH3:24])[CH3:23]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:22]([O:26][C:27](=[O:40])[N:28]([CH3:29])[C:30]1[C:31]2[N:32]([C:36]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=3)=[CH:37][N:38]=2)[CH:33]=[CH:34][N:35]=1)([CH3:25])([CH3:24])[CH3:23]

参加物

5

反応物 2

HCID 27632612-(Methylthio)-4-(tributylstannyl)pyrimidineHCID 58818944(3-Bromo-imidazo[1,2-a]pyrazin-8-yl)-methyl-carbamic acid tert-butyl ester

生成物 1

HCID 68226929Methyl-[3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 1140Toluene溶媒

実験手順

2-Methylsulfanyl-4-tributylstannanyl-pyrimidine (19.1 g, 46.0 mmol) was stirred in degassed toluene (achieved by bubbling nitrogen though solvent for 2 hours) (200 mL) under nitrogen, then (3-bromo-imidazo[1,2-a]pyrazin-8-yl)-methyl-carbamic acid tert-butyl ester (13.1 g, 40.0 mmol) (from Example 7 supra) was added followed by bis(triphenylphosphine)palladium (II) chloride (1.12 g, 1.60 mmol) and the reaction was heated at reflux. The reaction was cooled to room temperature and concentrated to dryness. The residue was purified by column chromatography on silica gel (petroleum ether to EtOAc, TLC Rf=0.17, 20% EtOAc in petroleum ether) and then triturated with DIPE to give methyl-[3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-carbamic acid tert-butyl ester. (Yield 8.00 g, 54%).

後処理

  1. temperaturethe reaction was heated
  2. temperatureat reflux
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by column chromatography on silica gel (petroleum ether to EtOAc, TLC Rf=0.17, 20% EtOAc in petroleum ether)
  5. customtriturated with DIPE

出典と根拠

ORDレコード
ord-21a62a00dcdf4f3c84dfd6684f068520
出典データセット
uspto-grants-2014_03
特許番号
US08673905B2

関連ノート

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