1,4-Dioxa-8-azaspiro(4.5)decane → HCID 57460954, compound

HRID 1674300Notes

Reaction equation

HRID 1674300 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[C:23]([C:28]#[N:29])=[CH:24][CH:25]=[CH:26][CH:27]=4)=[CH:18][CH:17]=3)=[C:11]([CH2:30][CH2:31][CH3:32])[N:10]=[C:9]2[CH2:33][CH3:34])=[CH:4][CH:3]=1.[O:35]1[C:39]2([CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[O:38][CH2:37][CH2:36]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:35]1[C:39]2([CH2:44][CH2:43][N:42]([C:2]3[CH:7]=[CH:6][C:5]([N:8]4[C:13](=[O:14])[C:12]([CH2:15][C:16]5[CH:21]=[CH:20][C:19]([C:22]6[C:23]([C:28]#[N:29])=[CH:24][CH:25]=[CH:26][CH:27]=6)=[CH:18][CH:17]=5)=[C:11]([CH2:30][CH2:31][CH3:32])[N:10]=[C:9]4[CH2:33][CH3:34])=[CH:4][CH:3]=3)[CH2:41][CH2:40]2)[O:38][CH2:37][CH2:36]1

Participants

7

Reactant 3

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 23676156Sodium t-butoxideHCID 57460953HCID 57460953, compound

Product 1

HCID 57460954HCID 57460954, compoundYield 61.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4′-{[1-(4-bromophenyl)-2-ethyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile (1.6 g), 1,1′-binaphthalene-2,2′-diylbis(diphenylphosphine) (0.29 g), 1,4-dioxa-8-azaspiro[4.5]decane (0.9 g) and sodium tert-butoxide (0.45 g) in toluene (40 mL) was added tris(dibenzylideneacetone)dipalladium (0.14 g), and the mixture was stirred at 100° C. for 12 hr under an argon atmosphere. The reaction mixture was diluted with ethyl acetate, and the insoluble material was filtered off through celite. The filtrate was washed with 1 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless solid (1.1 g, 60%).

Workup

  1. filtrationthe insoluble material was filtered off through celite
  2. washThe filtrate was washed with 1 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2974c6b0cb9f4246a4aec952229669c3
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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