Acetic Acid → 2-methylsulfanyl-3H-thieno[2,3-d]pyrimidin-4-one

HRID 269856

Reaktionsgleichung

Reaktionsgleichung von HRID 269856
[S:1]=[C:2]1[NH:7][C:6]2[S:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[NH:3]1.CI.[C:14](O)(=O)C>[OH-].[Na+]>[CH3:14][S:1][C:2]1[NH:3][C:4](=[O:11])[C:5]2[CH:10]=[CH:9][S:8][C:6]=2[N:7]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 36033932-sulfanyl-3H,4H-thieno(2,3-d)pyrimidin-4-one

Produkt 1

HCID 38520912-methylsulfanyl-3H-thieno[2,3-d]pyrimidin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-thioxo-2,3-dihydro-1H-thieno[2,3-d]pyrimidin-4-one (25.4 g, 0.138 mol) in 1N aqueous NaOH (600 mL) at room temperature was added methyl iodide (10.3 mL, 1.2 eq). The resulting mixture was stirred vigorously for about 2.5 hours. The reaction mixture was cooled to 0° C. and acetic acid was added (about 80 mL) until about pH=4.5 was reached. A fine precipitate was filtered and dried overnight to afford the title compound as a fine tan powder (24.8 g) (M+=198, M.P.=231.6-235.0° C.).

Aufarbeitung

  1. filtrationA fine precipitate was filtered
  2. customdried overnight

Quellen und Nachweise

ORD-Eintrag
ord-2b0484fd0ed1495ea3cc2857c7e24776
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449472B2

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