Sodium borohydride → 3-{1-[6-Ethoxy-7-(2-hydroxyethyl)oxy-2-morpholino-4-quinazolinyl]-4-piperidinyl}-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxoquinazoline

HRID 617165Notes

Reaction equation

HRID 617165 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH2:15][C:16](OCC)=[O:17])[N:10]=[C:9]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)[N:8]=[C:7]2[N:27]1[CH2:32][CH2:31][CH:30]([N:33]2[C:42](=[O:43])[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([CH3:44])[CH:40]=3)[N:35]([CH3:45])[C:34]2=[O:46])[CH2:29][CH2:28]1)[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][OH:17])[N:10]=[C:9]([N:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1)[N:8]=[C:7]2[N:27]1[CH2:32][CH2:31][CH:30]([N:33]2[C:42](=[O:43])[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([CH3:44])[CH:40]=3)[N:35]([CH3:45])[C:34]2=[O:46])[CH2:29][CH2:28]1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21851274HCID 21851274, compound

Product 1

HCID 218512323-{1-[6-Ethoxy-7-(2-hydroxyethyl)oxy-2-morpholino-4-quinazolinyl]-4-piperidinyl}-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxoquinazolineYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 20 ml of ethanol was dissolved 2.10 g (3.32 mmol) of Compound 54 obtained in Example 54, excess sodium borohydride was added, and the mixture was stirred under heating at reflux for 1 hour. After cooling, the solvent was removed, water was added and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with sodium chloride solution, dried and concentrated to give residue. The residue was purified by silica gel column chromatography(eluent: chloroform/methanol=100/1) and recrystallized from ethanol to give 1.29 g (yield: 66%) of Compound 55 as white crystals.

Workup

  1. additionwas added
  2. temperatureunder heating
  3. temperatureat reflux for 1 hour
  4. temperatureAfter cooling
  5. customthe solvent was removed
  6. additionwater was added
  7. extractionthe mixture was subjected to extraction with ethyl acetate
  8. washThe organic layer was washed with sodium chloride solution
  9. customdried
  10. concentrationconcentrated
  11. customto give residue
  12. customThe residue was purified by silica gel column chromatography(eluent
  13. customchloroform/methanol=100/1) and recrystallized from ethanol

Sources & evidence

ORD record
ord-3c8090a8b30f414f90631b8ff8e7bc4d
Source dataset
uspto-grants-1999_09
Patent number
US05948784

Reaction notes

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