Water → 6-chloro-3-methylpyrimidine-2,4(1H,3H)-dione

HRID 1773331

Reaktionsgleichung

Reaktionsgleichung von HRID 1773331
O.[CH3:2][N:3]1[C:8](=[O:9])[CH2:7][C:6](=O)[NH:5][C:4]1=[O:11].O=P(Cl)(Cl)[Cl:14]>>[Cl:14][C:6]1[NH:5][C:4](=[O:11])[N:3]([CH3:2])[C:8](=[O:9])[CH:7]=1

Komponenten

4

Edukt 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 757221-Methyl-2,4,6(1H,3H,5H)-pyrimidinetrione

Produkt 1

HCID 961416-chloro-3-methylpyrimidine-2,4(1H,3H)-dioneAusbeute 71,6 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Water (2.7 mL) is added dropwise to a suspension of 1-methylpyrimidine-2,4,6(1H,3H,5H)-trione (14.2 g, 100 mol) in POCl3 (95 mL) at 0° C. The reaction mixture is then heated at 80° C. for 5 hours. The resulting brownish solution is cooled, and POCl3 is evaporated under reduced pressure. The residue is treated with MeOH, and the obtained solid is recrystallized from ethanol to give 11.5 g product (Yield: 71.6%). m.p.=279-282° C. (dec) [Lit.2: 280-282° C.]. 1H NMR (400 MHz, DMSO-d6) δ3.10 (S, 3H), 5.90 (S, 1H), 12.4 (br, 1H).

Aufarbeitung

  1. temperatureThe resulting brownish solution is cooled
  2. customPOCl3 is evaporated under reduced pressure
  3. additionThe residue is treated with MeOH
  4. customthe obtained solid is recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-8cdfce3fbab8447db49365dae93cabe6
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255099B2

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