4-Iodo-2-(methylthio)pyrimidine → N-{1-Methyl-2-[4-(2-methylsulfanyl-pyrimidin-4-ylethynyl)-phenyl]-ethyl}acetamide

HRID 76193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 76193
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:5][CH:4]=1)#[CH:2].I[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([S:23][CH3:24])[N:18]=1>C(N)(CC)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:11][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[C:2][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([S:23][CH3:24])[N:18]=2)=[CH:4][CH:5]=1

Komponenten

6

Edukt 2

HCID 38589014-Iodo-2-(methylthio)pyrimidineHCID 86669621N-(1-(4-ethynylphenyl)propan-2-yl)acetamide

Produkt 1

HCID 66611369N-{1-Methyl-2-[4-(2-methylsulfanyl-pyrimidin-4-ylethynyl)-phenyl]-ethyl}acetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 24874Sec-ButylamineLösungsmittel

Versuchsvorschrift

To 0.52 g (2.58 mmol) N-[2-(4-ethynyl-phenyl)-1-methyl-ethyl]-acetamide (I58.3) and 0.50 g (1.98 mmol) 4-iodo-2-(methylthio)pyrimidine in 3 mL sec-butylamine and 3 mL water are added 0.14 g (0.20 mmol) bis(triphenylphosphine)dichloro-palladium and the mixture is stirred at r.t. over night. The reaction mixture is diluted with water and extracted with DCM. The organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel, DCM/MeOH 96/4). The resulting product is triturated with diethylether.

Aufarbeitung

  1. extractionextracted with DCM
  2. dry with materialThe organic layer is dried with Na2SO4
  3. customthe solvent is removed in vacuo
  4. customThe residue is purified by column chromatography (silica gel, DCM/MeOH 96/4)
  5. customThe resulting product is triturated with diethylether

Quellen und Nachweise

ORD-Eintrag
ord-81d7551219d24e2784d8aa15c266cd1c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835472B2

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