Dimethyl Sulfate → HCID 70004538, compound

HRID 580899Notes

Reaction equation

HRID 580899 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.Cl.O[C:10]1[C:15]2=[N:16][C:17]([CH3:24])=[C:18]([CH2:21][CH2:22][OH:23])[C:19](=[O:20])[N:14]2[CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>O>[OH:23][CH2:22][CH2:21][C:18]1[C:19](=[O:20])[N:14]2[CH:13]=[CH:12][CH:11]=[C:10]([O:6][CH3:7])[C:15]2=[N:16][C:17]=1[CH3:24]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 46852369HCID 46852369, compound

Product 1

HCID 70004538HCID 70004538, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethyl sulfate (2.52 g) was added dropwise to a mixture of intermediate 9 (4.4 g) and sodium hydroxide (0.8 g) in water (10 ml), while cooling in ice water. The reaction mixture was stirred for 15 minutes at RT, then it was heated for 1 hour using a warm water bath. The reaction mixture was cooled and extracted with CH2Cl2. The precipitate in the separated aqueous layer was filtered off and purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 97/3). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from CH3CN. The crystals were filtered off and dried, yielding 2 g (42%) of 3-(2-hydroxyethyl)-9-methoxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (intermediate 10).

Workup

  1. temperatureit was heated for 1 hour
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with CH2Cl2
  4. filtrationThe precipitate in the separated aqueous layer was filtered off
  5. custompurified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 97/3)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated
  8. customThe residue was crystallized from CH3CN
  9. filtrationThe crystals were filtered off
  10. customdried

Sources & evidence

ORD record
ord-4310c12bec8d4cfca5164fd6c581ebd4
Source dataset
uspto-grants-1999_07
Patent number
US05919788

Reaction notes

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