Tributylstannane → HCID 178441857, compound

HRID 1975445Notes

Reaction equation

HRID 1975445 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10](I)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].C([SnH](CCCC)CCCC)CCC.[O:30]1CCC[CH2:31]1>CN(C)C=O.C1(C)C=CC=CC=1.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([CH:31]=[O:30])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 3

HCID 5948TributylstannaneHCID 8028TetrahydrofuranHCID 178441862HCID 178441862, compound

Product 1

HCID 178441857HCID 178441857, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1.0 g of 2-butyl-6-iodo-4(1H)-quinazolinone and 0.355 g of tetrakis(triphenylphosphine)palladium in 15 ml of tetrahydrofuran and 5 ml of N,N-dimethylformamide, heated to 55° C. under an atmosphere of carbon monoxide is added a solution of 1.40 g of tri-n-butyltin hydride in 2.5 ml of toluene over 6 hours via a syringe pump. After the addition is complete the reaction is allowed to cool to room temperature, diluted with brine and extracted with chloroform. The combined organics are concentrated in vacuo and the resulting residue triturated with ether. The precipitate is collected by filtration and purified by flash chromatography on silica gel, eluting with 1:1 ethyl acetate-hexanes to give 0.35 g of the desired product, m.p. 242°-244° C.

Workup

  1. additionAfter the addition
  2. extractionextracted with chloroform
  3. concentrationThe combined organics are concentrated in vacuo
  4. customthe resulting residue triturated with ether
  5. filtrationThe precipitate is collected by filtration
  6. custompurified by flash chromatography on silica gel
  7. washeluting with 1:1 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-0db60c6ef62046348062f13fbdc72f80
Source dataset
uspto-grants-1994_02
Patent number
US05286729

Reaction notes

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