Hydrochloric Acid → HCID 19423337, compound

HRID 742973Notes

Reaction equation

HRID 742973 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:5]=2[N:4]([CH2:14][CH2:15][O:16]C2CCCCO2)[C:3]1=[O:23].Cl.[OH-].[Na+]>O>[OH:16][CH2:15][CH2:14][N:4]1[C:5]2[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][C:6]=2[C:7](=[O:8])[N:2]([CH3:1])[C:3]1=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 194233503,6-dimethyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione

Product 1

HCID 19423337HCID 19423337, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3 g of 3,6-dimethyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione were dissolved in 150 ml of water and the pH was adjusted to 1 with conc. hydrochloric acid at 20°-25° C., with stirring. After stirring for 5 h at room temperature, 2 N sodium hydroxide solution was added dropwise to pH 8 and the reaction mixture was concentrated under reduced pressure. After azeotropic drying with ethanol, the residue was purified by chromatography on silica gel in a medium-pressure column with dichloromethane/methanol (volume ratio 85:15) and by recrystallization from dichloromethane/diethyl ether.

Workup

  1. stirringAfter stirring for 5 h at room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dry with materialAfter azeotropic drying with ethanol
  4. customthe residue was purified by chromatography on silica gel in a medium-pressure column with dichloromethane/methanol (volume ratio 85:15) and by recrystallization from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-bfaf5713db3347f1a817b5c6991f6b0c
Source dataset
uspto-grants-1996_09
Patent number
US05556854

Reaction notes

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