Acetone → 2-phenyl-1-[2-(3,4,5-trimethoxy-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethanone

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Reaktionsgleichung

[C:1]1([C:7]#[C:8][C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)[N:16]=3)[NH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.C1(C)C=CC(S(O)(=O)=[O:38])=CC=1.CO.CC(C)=O>C(OCC)(=O)C>[C:1]1([CH2:7][C:8]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:19]=[C:20]([O:28][CH3:29])[C:21]([O:26][CH3:27])=[C:22]([O:24][CH3:25])[CH:23]=4)[N:16]=3)[NH:11][CH:10]=2)=[O:38])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

7-Phenylethynyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine (405 mg, 1.05 mmol) and p-toluenesulfonic acid monohydrate (40 mg, 0.21 mmol) were placed in a 20 ml microwave vial with 14 ml of a 2:1 mixture of methanol and acetone. The reaction was heated in a microwave reactor at 100° C. for 1.5 hours. The reaction was diluted with ethyl acetate, washed two times with saturated sodium bicarbonate and water, dried and concentrated. The residue was triturated with ethyl acetate and hexanes, filtered, and dried to yield 175 mg of 2-phenyl-1-[2-(3,4,5-trimethoxy-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethanone. MS: (M+H)+=404. MP=226.0-227.0° C.

Aufarbeitung

washwashed two times with saturated sodium bicarbonate and water
customdried
concentrationconcentrated
customThe residue was triturated with ethyl acetate and hexanes
filtrationfiltered
customdried

Quellen und Nachweise

ORD-Eintrag: ord-cc30a89aa5a14234b1695b5f6d3c0b00
Quelldatensatz: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08008298B2

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