Methanol → 3-[1-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-6-(1-hydroxyethyl)-1-methyl-2,4-dioxoquinazoline

HRID 1451915Notes

Reaction equation

HRID 1451915 reaction equation
CO.C(Cl)(Cl)Cl.[C:7]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[C:15](=[O:21])[N:14]([CH:22]1[CH2:27][CH2:26][N:25]([C:28]3[C:37]4[C:32](=[CH:33][C:34]([O:40][CH3:41])=[C:35]([O:38][CH3:39])[CH:36]=4)[N:31]=[CH:30][N:29]=3)[CH2:24][CH2:23]1)[C:13]2=[O:42])(=[O:9])[CH3:8].[BH4-].[Na+]>O>[CH3:39][O:38][C:35]1[CH:36]=[C:37]2[C:32](=[CH:33][C:34]=1[O:40][CH3:41])[N:31]=[CH:30][N:29]=[C:28]2[N:25]1[CH2:26][CH2:27][CH:22]([N:14]2[C:13](=[O:42])[C:12]3[C:17](=[CH:18][CH:19]=[C:10]([CH:7]([OH:9])[CH3:8])[CH:11]=3)[N:16]([CH3:20])[C:15]2=[O:21])[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 229233736-Acetyl-3-[1-(6,7-dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-quinazoline

Product 1

HCID 229235413-[1-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-6-(1-hydroxyethyl)-1-methyl-2,4-dioxoquinazolineYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

In a solvent mixture of 3ml of methanol and 3 ml of chloroform was dissolved 200.0 mg (0.41 mmol) of Compound 63 obtained in Example 50, and sodium borohydride was added thereto in excess, followed by heating at 60° C. for 30 minutes. After cooling, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed and dried, and the solvent was distilled off under reduced pressure. To the residue was added ether, and the precipitated crystals were collected by filtration and dried to give 146.4 mg (yield: 73%) of Compound 60 as white crystals.

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed
  5. customdried
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionTo the residue was added ether
  8. filtrationthe precipitated crystals were collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-66abfea0d23e420eb78b13e41f0a4795
Source dataset
uspto-grants-1997_02
Patent number
US05605900

Reaction notes

Loading…