Triethylamine → 6-[Allyl(methyl)amino]-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

HRID 42701

Reaktionsgleichung

Reaktionsgleichung von HRID 42701
Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]=[O:13].C(N(CC)CC)C.[CH3:21][NH:22][CH2:23][CH:24]=[CH2:25]>C(O)C>[CH2:23]([N:22]([CH3:21])[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]=[O:13])[CH:24]=[CH2:25]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 69391N-MethylallylamineHCID 3199716-Chloro-5-formyl-1,3-dimethyluracil

Produkt 1

HCID 866586896-[Allyl(methyl)amino]-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 6-chloro-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde (0.500 g, 2.47 mmol) and triethyl-amine (0.52 ml, 3.71 mmol) in dry ethanol (10 ml), N-methylprop-2-en-1-amine (0.36 ml, 3.71 mmol) was added under argon. The resulting mixture was stirred at room temperature under argon overnight. After evaporation of the solvent in vacuo, water (15 ml) was added to the yellow oily residue, and the mixture was extracted with dichloromethane (4×15 ml). The combined organic phases were dried over anhydrous MgSO4. The solvent was evaporated in vacuo, and the crude product was purified by crystallization from a mixture of cyclohexane:isopropyl alcohol (4:1).

Aufarbeitung

  1. customAfter evaporation of the solvent in vacuo, water (15 ml)
  2. additionwas added to the yellow oily residue
  3. extractionthe mixture was extracted with dichloromethane (4×15 ml)
  4. dry with materialThe combined organic phases were dried over anhydrous MgSO4
  5. customThe solvent was evaporated in vacuo
  6. customthe crude product was purified by crystallization from a mixture of cyclohexane:isopropyl alcohol (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-cc7929173e2d446b981067cd1f9e794d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536210B2

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