Selenium Dioxide → 2-Chloro-pyrimidine-4,6-dicarboxylic acid monomethyl ester

HRID 881895Notes

Reaction equation

HRID 881895 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=C(C)[N:3]=1.[Se](=O)=[O:14].O1[CH2:21][CH2:20][O:19][CH2:18]C1>>[CH3:18][O:19][C:20]([C:21]1[CH:5]=[C:6]([C:8]([OH:10])=[O:9])[N:7]=[C:2]([Cl:1])[N:3]=1)=[O:14]

Participants

4

Reactant 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 2736835Methyl 2-chloro-6-methylpyrimidine-4-carboxylate

Product 1

HCID 594607482-Chloro-pyrimidine-4,6-dicarboxylic acid monomethyl ester

Conditions

Temperature
105 °C

Procedure

To a stirred solution of methyl 2-chloro-6-methylpyrimidine-4-carboxylate (3.73 g, 20 mmol.) in dioxane (20 mL) is added selenium dioxide (3.55 g, 32 mmol) and the mixture is heated at 105° C. for 12 hours. The suspension is filtered through Celite and washed well with dioxane. The solvent is removed under reduced pressure to give 2-chloro-pyrimidine-4,6-dicarboxylic acid monomethyl ester; HPLC Retention time 0.65 minutes (condition A); MS 217.2 (M+1).

Workup

  1. filtrationThe suspension is filtered through Celite
  2. washwashed well with dioxane
  3. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-27ef427c1f6b40b2814490cb63eb41c7
Source dataset
uspto-grants-2015_03
Patent number
US08993631B2

Reaction notes

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