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

HRID 2389516Notes

Reaction equation

HRID 2389516 reaction equation
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

Participants

4

Reactant 3

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

Product 1

HCID 961416-chloro-3-methylpyrimidine-2,4(1H,3H)-dioneYield 71.6%

Conditions

Temperature
80 °C

Procedure

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) δ 3.10 (S, 3H), 5.90 (S, 1H), 12.4 (br, 1H).

Workup

  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

Sources & evidence

ORD record
ord-a613d8563c9e40d3b771323cf26b1883
Source dataset
uspto-grants-2012_09
Patent number
US08273750B2

Reaction notes

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