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Cerium(III) chloride → 3-[1-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-6-(2-hydroxy-2-propyl)-1-methyl-2,4-dioxoquinazoline

HRID 55054
Notes
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Reaction equation

HRID 55054 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[CH3:5][Mg]Br.[C:8]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH3:21])[C:16](=[O:22])[N:15]([CH:23]1[CH2:28][CH2:27][N:26]([C:29]3[C:38]4[C:33](=[CH:34][C:35]([O:41][CH3:42])=[C:36]([O:39][CH3:40])[CH:37]=4)[N:32]=[CH:31][N:30]=3)[CH2:25][CH2:24]1)[C:14]2=[O:43])(=[O:10])[CH3:9].[Cl-].[NH4+]>C1COCC1>[CH3:40][O:39][C:36]1[CH:37]=[C:38]2[C:33](=[CH:34][C:35]=1[O:41][CH3:42])[N:32]=[CH:31][N:30]=[C:29]2[N:26]1[CH2:27][CH2:28][CH:23]([N:15]2[C:14](=[O:43])[C:13]3[C:18](=[CH:19][CH:20]=[C:11]([C:8]([OH:10])([CH3:5])[CH3:9])[CH:12]=3)[N:17]([CH3:21])[C:16]2=[O:22])[CH2:24][CH2:25]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24636Cerium(III) chlorideHCID 25517Ammonium ChlorideHCID 229233736-Acetyl-3-[1-(6,7-dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-quinazolineHCID 178418573HCID 178418573, compound

Product 1

HCID 544677233-[1-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-6-(2-hydroxy-2-propyl)-1-methyl-2,4-dioxoquinazoline
Yield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 3 ml of THF was suspended 246.5 mg (1.0 mmol) of thoroughly dried cerium chloride, and 1 ml of a 1M solution of methylmagnesium bromide in THF was added thereto under an argon gas atmosphere, followed by stirring at room temperature for 1 hour. To the reaction mixture was dropwise added a solution of 245.0 mg (0.50 mmol) of Compound 63 obtained in Example 50 in 5 ml of THF, and the mixture was stirred at room temperature for 3 hours. A saturated aqueous solution of ammonium chloride was added thereto in excess to stop the reaction, followed by extraction with chloroform. The organic layer was washed and dried, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=100/1) and recrystallized from ether to give 78.8 mg (yield: 31%) of Compound 61 as white crystals.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. customthe reaction
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed
  6. customdried
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=100/1)
  9. customrecrystallized from ether

Sources & evidence

ORD record
ord-28297d47bde84f4a8b598c8d9b1032aa
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05624926

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes