Hydrochloric Acid → 6-(4-Hydroxybutyl)-3-methyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione

HRID 742972Notes

Reaction equation

HRID 742972 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[CH2:9][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][O:17]C3CCCCO3)[CH2:11][CH2:12][C:5]=2[NH:4][C:3]1=[O:24].O.Cl>CO>[OH:17][CH2:16][CH2:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][C:5]2[NH:4][C:3](=[O:24])[N:2]([CH3:1])[C:7](=[O:8])[C:6]=2[CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 194233293-methyl-6-[4-(tetrahydropyran-2-yloxy)butyl]-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione

Product 1

HCID 194233386-(4-Hydroxybutyl)-3-methyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

12 g of 3-methyl-6-[4-(tetrahydropyran-2-yloxy)butyl]-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione were dissolved in 150 ml of methanol and 150 ml of water and the pH was adjusted to i with conc. hydrochloric acid at 20°-25° C., with stirring. After 7 h at room temperature, the mixture was concentrated to dryness under reduced pressure, the residue was taken up with water and the solution was adjusted to pH 7.8. It was concentrated under vacuum and the residue was extracted exhaustively with hot ethanol. The ethanolic extract was evaporated under reduced pressure and the crude 6-(4-hydroxybutyl)-3-methyl-5,6,7,8-tetrahydro-1H-pyrido-[4,3-d]pyrimidine-2,4-dione was purified by column chromatography on silica gel with dichloromethane/methanol (volume ratio 90:10) and by recrystallization from isopropanol.

Workup

  1. concentrationthe mixture was concentrated to dryness under reduced pressure
  2. concentrationIt was concentrated under vacuum
  3. extractionthe residue was extracted exhaustively with hot ethanol
  4. extractionThe ethanolic extract
  5. customwas evaporated under reduced pressure
  6. customthe crude 6-(4-hydroxybutyl)-3-methyl-5,6,7,8-tetrahydro-1H-pyrido-[4,3-d]pyrimidine-2,4-dione was purified by column chromatography on silica gel with dichloromethane/methanol (volume ratio 90:10) and by recrystallization from isopropanol

Sources & evidence

ORD record
ord-48683d181c36403fa8e52779b6e02e28
Source dataset
uspto-grants-1996_09
Patent number
US05556854

Reaction notes

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