N-bromobutanimide → 6-Amino-5-bromo-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 585037Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 585037
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[NH:5][C:4](=[O:10])[CH:3]=1.[Br:11]N1C(=O)CCC1=O>CN(C=O)C>[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[NH:5][C:4](=[O:10])[C:3]=1[Br:11]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 755206-Amino-1-methyluracil

Produkt 1

HCID 2554456-Amino-5-bromo-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dioneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 6-amino-1-methyluracil (14.0 g, 100 mmol), N-bromosuccinimide (21.0 g, 118 mmol), and dry DMF (250 mL) was heated at 80° C. for 3 h. The reaction mixture was evaporated in vacuo and the residue was slurried with ice-cold 50% aqueous ethanol (150 mL) and filtered. The resulting off-white solid was washed with ethanol, then ether and dried to yield 18.0 g 2a (83%). mp 274° C. dec; UV pH 1 λmax 276 nm; NMR δ (DMSO-d6) 3.26 (s, 3H, CH3), 7.02 (s, 2H, NH2), 10.89 (s, 1H, NH).

Aufarbeitung

  1. customThe reaction mixture was evaporated in vacuo
  2. filtrationfiltered
  3. washThe resulting off-white solid was washed with ethanol
  4. dry with materialether and dried

Quellen und Nachweise

ORD-Eintrag
ord-3c524e69c53c4b8a83fb137e26ed6f5b
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06930101B1

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