Ethanol → HCID 58458909, compound

HRID 390337Notes

Reaction equation

HRID 390337 reaction equation
O[Li].O.[CH2:4]([O:11][C:12]1[C:17](=[O:18])[N:16]([CH3:19])[C:15](SC)=[N:14][C:13]=1[C:22]([O:24]CC)=[O:23])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:27][CH2:28][OH:29]>>[CH2:4]([O:11][C:12]1[C:17](=[O:18])[N:16]([CH3:19])[C:15]([O:29][CH2:28][CH3:27])=[N:14][C:13]=1[C:22]([OH:24])=[O:23])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 21060064HCID 21060064, compound

Product 1

HCID 58458909HCID 58458909, compoundYield 99%

Procedure

To a stirred solution of LiOH.H2O (1.26 g, 30 mmol) in EtOH (100 mL) at 40° C. was added ethyl 5-(benzyloxy)-1-methyl-2-(methylthio)-6-oxo-1,6-dihydropyrimidine-4-carboxylate (prepared according to the procedure in WO2004062613) (6.7 g, 20 mmol). The resulting reaction mixture was stirred at room temperature for 5 h then concentrated. The residue was taken up in aq. HCl (50 mL) and extracted with EtOAc (2×100 mL). The combined organic fractions were dried (Na2SO4), filtered and concentrated to give the desired product (6 g, 99% yield) as off-white solid which was used in the next step without purification.

Workup

  1. customprepared
  2. customThe resulting reaction mixture
  3. concentrationthen concentrated
  4. extractionextracted with EtOAc (2×100 mL)
  5. dry with materialThe combined organic fractions were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d1207ad9408a4824bfb74d29662b0483
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

Loading…