Phosphonium → HCID 178435592, compound

HRID 1708470Notes

Reaction equation

HRID 1708470 reaction equation
[CH2:1]([Li])CCC.[PH4+].[CH2:7]([C:11]1[NH:12][C:13]2[C:18]([C:19](=[O:21])[N:20]=1)=[CH:17][C:16]([CH:22]=O)=[CH:15][CH:14]=2)[CH2:8][CH2:9][CH3:10]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:7]([C:11]1[NH:12][C:13]2[C:18]([C:19](=[O:21])[N:20]=1)=[CH:17][C:16]([CH:22]=[CH2:1])=[CH:15][CH:14]=2)[CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 5460504PhosphoniumHCID 178418339ButyllithiumHCID 178441857HCID 178441857, compound

Product 1

HCID 178435592HCID 178435592, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a suspension of 15.14 g of methyltriphenylphosphonium bromide in tetrahydrofuran, cooled to -78° C., is slowly added 21.73 ml of 1.95M n-butyllithium in hexanes. The reaction mixture is allowed to warm to room temperature and stirred until all of the phosphonium salt dissolves. This takes approximately 30 minutes. The reaction mixture is cooled to -78° C. and 1.95 g of 2-butyl-1,4-dihydro-4-oxo-6-quinazolinecarboxaldehyde added in one portion as a solid. The reaction mixture is allowed to warm to room temperature and stirred for 18 hours. The reaction mixture is quenched with saturated ammonium chloride, diluted with water and extracted with ethyl acetate. The organic layer is separated, washed with brine, dried with MgSO4 and concentrated in vacuo to a residue which is purified by chromatography on silica gel using 1:3 ethyl acetate-hexanes to give 2.48 g of the desired product as a solid. CI mass spec 229 (M+H).

Workup

  1. temperatureto warm to room temperature
  2. dissolutiondissolves
  3. customThis takes approximately 30 minutes
  4. temperatureThe reaction mixture is cooled to -78° C.
  5. temperatureto warm to room temperature
  6. customThe reaction mixture is quenched with saturated ammonium chloride
  7. additiondiluted with water
  8. extractionextracted with ethyl acetate
  9. customThe organic layer is separated
  10. washwashed with brine
  11. dry with materialdried with MgSO4
  12. concentrationconcentrated in vacuo to a residue which
  13. customis purified by chromatography on silica gel using 1:3 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-802a9cd4ef4c4548960ad6efcd5b44b9
Source dataset
uspto-grants-1994_10
Patent number
US05358951

Reaction notes

Loading…