Sodium Hydroxide → 2-methyl-4H-thiazolo[5,4-d]pyrimidine-5,7-dione

HRID 1919350Notes

Reaction equation

HRID 1919350 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH3:15])[S:9][C:10]=1[NH:11][C:12]([NH2:14])=[O:13])=O)C.[OH-].[Na+]>CC(O)C.O>[CH3:15][C:8]1[S:9][C:10]2[NH:11][C:12](=[O:13])[NH:14][C:4](=[O:3])[C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 582349302-Methyl-5-ureido-thiazole-4-carboxylic acid ethyl ester

Product 1

HCID 3456422-methyl-4H-thiazolo[5,4-d]pyrimidine-5,7-dioneYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 2-methyl-5-ureido-thiazole-4-carboxylic acid ethyl ester (21.0 g, 0.079 mol) in iPrOH (300 mL) was added an aqueous solution of NaOH (3 M, 26 mL, 0.078 mol) at 80° C. The thick white suspension was heated at 80° C. for 45 min, then diluted with H2O and cooled to 0° C. The reaction mixture was acidified to pH 3 and the precipitate collected by filtration. The white solid was washed with H2O and dried in vacuo at 60° C. for 17 h to give the title compound as a white solid (12.3 g, 83%).

Workup

  1. temperaturecooled to 0° C
  2. filtrationthe precipitate collected by filtration
  3. washThe white solid was washed with H2O
  4. customdried in vacuo at 60° C. for 17 h

Sources & evidence

ORD record
ord-de2893eca5de4b74a7ae2702ce2b12b3
Source dataset
uspto-grants-2012_05
Patent number
US08168633B2

Reaction notes

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