4-Methylpiperidine → 2-Chloro-7-methyl-4-(4-methylpiperidino)thieno[3,2-d]pyrimidine

HRID 1250631

Reaktionsgleichung

[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1.[CH3:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([N:17]2[CH2:18][CH2:19][CH:14]([CH3:13])[CH2:15][CH2:16]2)[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

In 10 ml of DMF was dissolved 1.0 g (4.6 mmol) of 2,4-dichloro-7-methylthieno[3,2-d]pyrimidine, and then 1.06 g (10.7 mmol) of 4-methylpiperidine was added dropwise to the resulting solution under ice cooling over 5 minutes. The reaction mixture was stirred at 0° C. for one hour and then allowed to resume to room temperature, followed by stirring for one hour. After completion of the reaction, ice water was added to the reaction mixture, followed by extraction with ethyl acetate (50 ml×3). After the organic layer was washed successively with 1N hydrochloric acid, water and brine and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/10) to give 1.20 g (yield: 93.3%) of the title compound.

Aufarbeitung

customto resume to room temperature
stirringby stirring for one hour
additionwas added to the reaction mixture
extractionfollowed by extraction with ethyl acetate (50 ml×3)
washAfter the organic layer was washed successively with 1N hydrochloric acid, water and brine
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/10)

Quellen und Nachweise

ORD-Eintrag: ord-64ecb0c4f947486599238ad569b6f601
Quelldatensatz: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06339089B2

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