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

HRID 1465972

Reaktionsgleichung

Reaktionsgleichung von HRID 1465972
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-90f3be5fd5034bcab06f57280a26cd6b
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000001B2

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