Methyl iodide → HCID 178503542, Verbindung

HRID 474741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 474741
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10](=[O:16])[NH:11][C:12](=[S:15])[NH:13][CH:14]=2)=[CH:4][N:3]=1.[CH3:17]C[O-].[Na+].CI>C(O)C>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][C:9]2[C:10](=[O:16])[N:11]=[C:12]([S:15][CH3:17])[NH:13][CH:14]=2)=[CH:6][N:7]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 2723922Sodium ethoxideHCID 205833715-(2-Methyl-pyrimidin-5-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

Produkt 1

HCID 178503542HCID 178503542, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

5-(2-Methyl-pyrimidin-5-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (210 mg, 234.28 gmol−1, 0.90 mmol, 1 eq) and NaOEt (2 eq, 128 mg) were stirred in 5 ml of absolute ethanol at room temperature for 30 minutes. In the suspension was then added methyl iodide (2.5 eq, 140 μl) and the mixture was stirred for 35 hours. Solvent was then evaporated. In the mixture was added 3 ml of water and pH was adjusted to 5-6 range using 3N HCl water solution. The resulting precipitate was collected and dried to afford 5-(2-methyl-pyrimidin-5-ylmethyl)-2-methylsulfanyl-1H-pyrimidin-4-one (85 mg, yield=36.6%, purity=96%) in form of white powder. MS: [M+H]+=249.22 1H NMR (300 MHz; DMSO-d6) δ/ppm 2.45 (s, 3H), 2.54 (s, 3H), 3.57 (s, 2H), 7.87 (br.s., 1H), 8.56 (s, 2H), 12.79 (br.s., 1H).

Aufarbeitung

  1. customSolvent was then evaporated
  2. additionIn the mixture was added 3 ml of water and pH
  3. customThe resulting precipitate was collected
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e0c8cd5a0c0a4f34adc49eb09d189c66
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637536B2

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