Methanesulfonic Acid → HCID 69959125, compound

HRID 379589Notes

Reaction equation

HRID 379589 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([S:9][CH2:10][C:11]([O:13]C)=O)[N:4]([CH3:15])[C:3]1=[O:16].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=O)[CH:18]=1.[OH-].[Na+].C(O[CH2:31][CH3:32])(=O)C.[CH3:33]S(O)(=O)=O>>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:11](=[O:13])[C:10](=[CH:23][C:19]3[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=3)[S:9][C:5]=2[N:4]([CH2:15][CH:31]([CH3:32])[CH3:33])[C:3]1=[O:16]

Participants

6

Reactant 5

HCID 6395Methanesulfonic AcidHCID 8857Ethyl AcetateHCID 103713-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 18366602HCID 18366602, compound

Product 1

HCID 69959125HCID 69959125, compound

Conditions

Temperature
110 °C

Procedure

Methyl 2-[(1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-4-pyrimidinyl)thio]acetate (2.83 g) and pyridine-3-carboxaldehyde (2.9 ml) were dissolved in methanesulfonic acid (28 ml) and the mixture was heated to 110° C. for 18 h. The reaction was allowed to cool and was then extracted thrice with dichloromethane. The organic phases were washed with sodium bicarbonate (aqueous) and brine, dried, filtered and evaporated to give a brown residue. The aqueous phase was made alkaline by addition of sodium hydroxide and was then extracted thrice with dichloromethane, the extracts were dried, filtered and evaporated to give a second crop. Chromatography of the two batches of impure product (eluent ethyl acetate) gave the subtitle compound (2.00 g).

Workup

  1. temperatureto cool
  2. extractionwas then extracted thrice with dichloromethane
  3. washThe organic phases were washed with sodium bicarbonate (aqueous) and brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto give a brown residue
  8. extractionwas then extracted thrice with dichloromethane
  9. customthe extracts were dried
  10. filtrationfiltered
  11. customevaporated
  12. customto give a second crop

Sources & evidence

ORD record
ord-44c67a570ab74155bb73c2a3e7ce10bf
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Reaction notes

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