Carbon Tetrachloride → HCID 18925055, compound

HRID 1288889Notes

Reaction equation

HRID 1288889 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][NH:7][C:6]2=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:34].[C:38]([C:40]1[CH:41]=[C:42]([CH:44]=[CH:45][CH:46]=1)[NH2:43])#[CH:39]>ClCCCl.C(O)(C)(C)C>[ClH:34].[C:38]([C:40]1[CH:41]=[C:42]([NH:43][C:6]2[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][N:7]=2)[CH:44]=[CH:45][CH:46]=1)#[CH:39]

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 104682Benzenamine, 3-ethynyl-HCID 1354514236-Methoxyquinazolin-4-OL

Product 1

HCID 18925055HCID 18925055, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

A 25 mM solution of 6-methoxy-3H-quinazolin-4-one in 1,2-dichloroethane was added to polymer-supported triphenylphosphine (from Fluka, about 3 mmol P/g polymer; 2.5 mol equiv) and carbon tetrachloride (100 mole equiv). The reaction mixture was heated, with shaking, at 60° C. for 21 hours, cooled to 22° C., and a 30 mM solution of the 3-ethynylaniline (1.5 mole equiv) in t-butanol was added. The resulting mixture was then heated, with shaking, at 60° C. for 18 hours followed by cooling to 22° C. The polymer was filtered off and washed twice with methanol. The methanol washes were added to the filtrate and the solution was concentrated in vacuo to afford the title product (73%; LC-MS: 276 (MH+); anal. RP18-HPLC RT: 5.82 min). For these cases the analytical RP18-HPLC system consisted of a Waters 717 (trademark) autosampler, Waters 996 Photodiode Array Detector (trademark), and Waters 600 quarternary solvent delivery system, and was controlled by Millennium (trademark) software. The aliquots of samples were chromatographed using a linear gradient of 0% to 100% acetonitrile/0.2M ammonium acetate buffer (pH 4.5) over ten minutes at a flow rate of 3 ml/min. using a Perkin-Elmer Pecosphere (trademark) (3 mm×3 cm) C18 column.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturecooled to 22° C.
  3. temperatureThe resulting mixture was then heated
  4. stirringwith shaking, at 60° C. for 18 hours
  5. temperatureby cooling to 22° C
  6. filtrationThe polymer was filtered off
  7. washwashed twice with methanol
  8. additionThe methanol washes were added to the filtrate
  9. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-77c17fb8b3514cdb80dcf5f90defcd61
Source dataset
uspto-grants-1998_05
Patent number
US05747498

Reaction notes

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