Ammonia → Ethyl 5-methyl-4-oxo-2-(thiophen-3-ylmethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

HRID 2066937

Reaktionsgleichung

Reaktionsgleichung von HRID 2066937
[NH2:1][C:2]1[S:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:4]([CH3:12])[C:3]=1[C:13]([O:15]CC)=O.[S:18]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]#[N:25])=[CH:19]1.Cl.O1CCOCC1.N>>[CH3:12][C:4]1[C:3]2[C:13](=[O:15])[NH:25][C:24]([CH2:23][C:20]3[CH:21]=[CH:22][S:18][CH:19]=3)=[N:1][C:2]=2[S:6][C:5]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Komponenten

5

Edukt 4

HCID 222AmmoniaHCID 78537Diethyl 5-amino-3-methylthiophene-2,4-dicarboxylateHCID 837303-ThienylacetonitrileHCID 204431481,4-Dioxane hydrochloride

Produkt 1

HCID 68664667Ethyl 5-methyl-4-oxo-2-(thiophen-3-ylmethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

Versuchsvorschrift

515 Milligrams of diethyl 5-amino-3-methylthiophene-2,4-dicarboxylate and 296 mg of 3-thiopheneacetonitrile were added to 8 mL of 4N hydrogen chloride-dioxane solution and stirred for 10 hours. Thereafter the liquid reaction mixture was poured on ice, and its pH was adjusted to 8-9 with 25% aqueous ammonia. Whereupon precipitated crystals were recovered by filtration and washed first with water, and then with hexane. The crude crystals were recrystallized from a liquid mixture of N,N-dimethylformamide and cyclohexane, to provide 397 mg of the title compound.

Aufarbeitung

  1. customThereafter the liquid reaction mixture
  2. additionwas poured on ice, and its pH
  3. customWhereupon precipitated crystals
  4. filtrationwere recovered by filtration
  5. washwashed first with water
  6. customThe crude crystals were recrystallized from a liquid mixture of N,N-dimethylformamide and cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-7ae2e1a642a94fbaaf7e00fb9956dc0f
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293754B2

Verknüpfte Notizen

Wird geladen…