Lithium Chloride → HCID 59351564, compound

HRID 1889415Notes

Reaction equation

HRID 1889415 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:5]2=[O:21].[CH2:22](C([Sn])=C(CCCC)CCCC)[CH2:23]CC.[Cl-].[Li+].[F-].[K+]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[C:15]1([CH2:14][CH2:13][N:6]2[C:5](=[O:21])[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([CH:22]=[CH2:23])[CH:3]=3)[NH:8][C:7]2=[O:12])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 53438229Tri(butyl)vinyltinHCID 59351595HCID 59351595, compound

Product 1

HCID 59351564HCID 59351564, compoundYield 322%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution (40 mL) of 6-iodo-3-(2-phenylethyl)quinazoline-2,4(1H,3H)-dione (2.0 g), tributylvinyltin (1.9 g), lithium chloride (1.1 g), dichlorobis(triphenylphosphine)palladium (0.18 g) in N,N-dimethylformamide was stirred under argon atmosphere at 90° C. for 12 hr. The reaction mixture was allowed to cool to room temperature, ethyl acetate and 15% potassium fluoride solution were added, and the mixture was stirred for 2 hr. Insoluble material was filtered off through celite. The organic layer of the filtrate was separated, washed with 1N hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a pale-yellow solid (4.8 g, 97%).

Workup

  1. filtrationInsoluble material was filtered off through celite
  2. customThe organic layer of the filtrate was separated
  3. washwashed with 1N hydrochloric acid and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-43980076023945d9937ae0fecac1fcec
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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