2-(Tributylstannyl)pyridine → 7-pyridin-2-yl-3H-quinazolin-4-one

HRID 968573Notes

Reaction equation

HRID 968573 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)CCC>C1(C)C=CC=CC=1.O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 1355556127-Bromo-3,4-dihydroquinazolin-4-one

Product 1

HCID 1356820597-pyridin-2-yl-3H-quinazolin-4-one

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 21840791Dioxane tolueneSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 7-bromo-3H-quinazolin-4-one (100 mg, 0.444 mmol) in toluene/dioxane (3:1), add 2-tributylstannanyl-pyridine (162 mg, 0.444 mmol) followed by tetrakis-(triphenylphosphine)-palladium(0) (26 mg, 0.022 mmol). Bubble dry nitrogen through the solution for 10 minutes then heat the stirring solution to 115° C. under a nitrogen atmosphere. After several minutes the reaction mixture becomes homogeneous. After 16 hours, cool the reaction vessel and collect the precipitate via filtration. Wash the solid with 25% EtOAc/hexanes followed by hexanes to give 7-pyridin-2-yl-3H-quinazolin-4-one as a beige solid.

Workup

  1. customBubble dry nitrogen through the solution for 10 minutes
  2. waitAfter several minutes the reaction mixture becomes homogeneous
  3. temperaturecool the reaction vessel
  4. customcollect the precipitate
  5. filtrationvia filtration
  6. washWash the solid with 25% EtOAc/hexanes

Sources & evidence

ORD record
ord-0e5e57aee81f4e3fb940b60b2a172e4e
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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