Tributylvinyltin → methyl 3-[4-[(2,4-difluorobenzyl)oxy]-6-oxo-5-vinylpyrimidin-1(6H)-yl]-4-methylbenzoate
Reaktionsgleichung
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[CH2:4][O:5][C:6]1[N:7]=[CH:8][N:9]([C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:17]([O:19][CH3:20])=[O:18])[C:10](=[O:13])[C:11]=1I.[CH2:30]([Sn](CCCC)(CCCC)C=C)[CH2:31]CC.[Sn]>CN(C)C=O.[Pd]>[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[CH2:4][O:5][C:6]1[N:7]=[CH:8][N:9]([C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:17]([O:19][CH3:20])=[O:18])[C:10](=[O:13])[C:11]=1[CH:30]=[CH2:31]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
A round bottom flask containing methyl 3-[4-[(2,4-difluorobenzyl)oxy]-5-iodo-6-oxopyrimidin-1(6H)-yl]-4-methylbenzoate (2.50 g, 4.88 mmol) in N, N-dimethylformamide was evacuated and flushed with argon. Tributyl(vinyl)tin (2.3 g, 7.3 mmol) and dichlorobis(triphenylphosphine) palladium (II) (0.34 g, 0.49 mmol) were added in the nitrogen atmosphere of a glove box. Heated at 60° C. under argon overnight. Added additional tin (0.7 mL) and palladium (0.17 g) reagents and continued over weekend. No progress observed. Distilled DMF, washed crude product with ethyl acetate, and filtered through celite. The filtrate was concentrated and purified by flash column using 25% ethyl acetate in hexane as eluent. Used without further purification.
Aufarbeitung
- customwas evacuated
- customflushed with argon
- waitcontinued over weekend
- washDistilled DMF, washed crude product with ethyl acetate
- filtrationfiltered through celite
- concentrationThe filtrate was concentrated
- custompurified by flash column
- customUsed without further purification
Quellen und Nachweise
- ORD-Eintrag
- ord-ed446d75674849aa989e0813bb7bfe65
- Quelldatensatz
- uspto-grants-2007_02
- Patentnummer
- US07183287B2
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