Methyl 3-oxovalerate → 5-ethyl-2-mercapto-3H-pyrano[2,3-d]pyrimidine-4,7-dione

HRID 2357876Notes

Reaction equation

HRID 2357876 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[N:5]=[C:4]([SH:9])[N:3]=1.[C:10]([CH2:14][C:15](OC)=[O:16])(=O)[CH2:11][CH3:12]>O>[CH2:11]([C:10]1[C:7]2[C:6](=[O:8])[NH:5][C:4](=[S:9])[NH:3][C:2]=2[O:1][C:15](=[O:16])[CH:14]=1)[CH3:12]

Participants

4

Reactant 2

HCID 121699Methyl 3-oxovalerateHCID 178516656HCID 178516656, compound

Product 1

HCID 533226895-ethyl-2-mercapto-3H-pyrano[2,3-d]pyrimidine-4,7-dioneYield 37.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4,6-dihydroxy-2-mercapto-pyrimidine (20.0 g, 138.7 mmol) and methyl propionylacetate (21.8 mL, 173.4 mmol) was heated at 165° C. until the ester was completely reacted. The reaction mixture was cooled down and poured into water (75 mL) and then filtered through a sintered funnel. The solid residue was washed with water (2×20 mL) and dried under vacuum to yield 5-ethyl-2-thioxo-2,3-dihydro-1h-pyrano[2,3-d]pyrimidine-4,7-dione (11.6 g, 37%).

Workup

  1. customwas completely reacted
  2. temperatureThe reaction mixture was cooled down
  3. filtrationfiltered through a sintered funnel
  4. washThe solid residue was washed with water (2×20 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d62789bdd174400d9486b7cb4ea4beee
Source dataset
uspto-grants-2010_07
Patent number
US07763623B2

Reaction notes

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