Methyl iodide → 4-Methylthiopyrido[4,3-d]pyrimidine

HRID 50776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 50776
[N:1]1[C:6]2[CH:7]=[CH:8][N:9]=[CH:10][C:5]=2[C:4](=[S:11])[NH:3][CH:2]=1.[CH2:12](N(CC)CC)C.IC>CS(C)=O>[CH3:12][S:11][C:4]1[C:5]2[CH:10]=[N:9][CH:8]=[CH:7][C:6]=2[N:1]=[CH:2][N:3]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 178527905HCID 178527905, Verbindung

Produkt 1

HCID 106548874-Methylthiopyrido[4,3-d]pyrimidineAusbeute 156,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of 3H-pyrido[4,3-d]pyrimidin-4-thione (676 mg, 4.14 mmol), triethylamine (1.4 mL, 10.31 mmol), DMSO (4 mL), and iodomethane (0.48 mL, 7.72 mmol) is stirred for 12 h under N2 at 25° C. The mixture is poured onto water and extracted with EtOAc. The organic extracts are dried (MgSO4), and the solvent is removed under reduced pressure to yield 4-methylthiopyrido[4,3-d]pyrimidine (1.15 g, quant.) as a brown solid. 1H NMR (DMSO) δ 9.52 (1H, s), 9.16 (1H, s), 8.95 (1H, d, J=6 Hz), 7.86 (1H, d, J=8 Hz), 2.75 (1H, s).

Aufarbeitung

  1. additionThe mixture is poured onto water
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts are dried (MgSO4)
  4. customthe solvent is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c94097e994344d5299ddc8bff6bdfbf6
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713484B2

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