2-Methylfuran → HCID 77107020, compound

HRID 2201227Notes

Reaction equation

HRID 2201227 reaction equation
[F:1][C:2]1([F:27])[CH:10](O)[C:9]2[N:5]([C:6]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)=[C:7]3[C:15](=[O:16])[N:14]([CH3:17])[C:13](=[O:18])[N:12]([CH3:19])[C:8]3=2)[CH2:4][CH2:3]1.[CH3:28][C:29]1[O:30][CH:31]=[CH:32][CH:33]=1>C(#N)C.[Au](Cl)(Cl)Cl>[F:27][C:2]1([F:1])[CH:10]([C:31]2[O:30][C:29]([CH3:28])=[CH:33][CH:32]=2)[C:9]2[N:5]([C:6]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)=[C:7]3[C:15](=[O:16])[N:14]([CH3:17])[C:13](=[O:18])[N:12]([CH3:19])[C:8]3=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 107972-MethylfuranHCID 86723462HCID 86723462, compound

Product 1

HCID 77107020HCID 77107020, compound

Reagents, catalysts & solvents 2

HCID 26030Gold trichlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

Gold (III) chloride (4 mg, 0.012 mmol) was added to a suspension of 9,9-difluoro-5-(3-fluorophenyl)-10-hydroxy-1,3-dimethyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione (47 mg, 0.12 mmol) and 2-methylfuran (15 μL, 0.16 mmol) in acetonitrile (1 mL). The mixture was stirred at room temperature for 1 hour. The mixture was evaporated under vacuum, the residue was dissolved in DCM (5 mL) and washed with water (5 mL). The organic phase was passed through a hydrophobic frit evaporated under vacuum. Purification by mass directed HPLC using the following conditions afforded the title compound.

Workup

  1. customThe mixture was evaporated under vacuum
  2. dissolutionthe residue was dissolved in DCM (5 mL)
  3. washwashed with water (5 mL)
  4. customevaporated under vacuum
  5. customPurification by mass

Sources & evidence

ORD record
ord-8ac1c6102fdf4f9fa8d8119e2155f3d9
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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