Triphenylphosphine → 1,2,3,4-Tetrahydro-3-methyl-2,4-dioxo5-trimethylsilylethynyl-quinazoline

HRID 1199646Notes

Reaction equation

HRID 1199646 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:14])[N:5]([CH3:13])[C:6](=[O:12])[NH:7]2.[CH3:15][Si:16]([C:19]#[CH:20])([CH3:18])[CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:13][N:5]1[C:4](=[O:14])[C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[C:20]#[C:19][Si:16]([CH3:18])([CH3:17])[CH3:15])[NH:7][C:6]1=[O:12]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 66111Trimethylsilylacetylene2×HCID 14460512HCID 14460512, compound

Product 1

HCID 144605131,2,3,4-Tetrahydro-3-methyl-2,4-dioxo5-trimethylsilylethynyl-quinazolineYield 46%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

To a degassed solution of 5-bromo-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-quinazoline (1.0 g, 4.0 mmol) in 20 ml of DMF and 20 ml of triethylamine was added trimethylsilylacetylene (1.6 ml, 12 mmol), 50 mg of triphenylphosphine, 20 mg of palladium(II)acetate, and 1 mg of cuprous(I)iodide. The mixture was stirred under nitrogen, at 70° C. After 7 h additionally 0.4 ml of trimethylsilylacetylene was added and heating continued for 4 h. Then the mixture was evaporated in vacuo and the residue extracted with 100 ml of dichloromethane and 100 ml of water. The organic layer was washed twice with 100 ml of water, dried over anhydrous sodium sulfate, treated with charcoal, filtered through a pad of celite, and evaporated. The residue was triturated with ether/petroleum ether (1:1) and filtered off and dried giving 0.50 g (46%) of 1,2,3,4-tetrahydro-3-methyl-2,4-dioxo-5-trimethylsilylethynyl-quinazoline.

Workup

  1. temperatureheating
  2. customThen the mixture was evaporated in vacuo
  3. extractionthe residue extracted with 100 ml of dichloromethane and 100 ml of water
  4. washThe organic layer was washed twice with 100 ml of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. additiontreated with charcoal
  7. filtrationfiltered through a pad of celite
  8. customevaporated
  9. customThe residue was triturated with ether/petroleum ether (1:1)
  10. filtrationfiltered off
  11. customdried

Sources & evidence

ORD record
ord-1997555397d94a988a3fc36d8a4e169d
Source dataset
uspto-grants-1990_02
Patent number
US04902686

Reaction notes

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