Diethyl Ether → HCID 11776699, compound

HRID 2210230Notes

Reaction equation

HRID 2210230 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8](CC1C=CC(OC)=CC=1)[C:7](=[O:21])[NH:6][C:5]2([CH:24]1[CH2:26][CH2:25]1)[C:22]#[CH:23].FC(F)(F)C(O)=O.CCOCC>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:21])[NH:6][C:5]2([CH:24]1[CH2:26][CH2:25]1)[C:22]#[CH:23]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 10406630HCID 10406630, compound

Product 1

HCID 11776699HCID 11776699, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.4 g (4.11 mmol) of 6-chloro-4-cyclopropyl-4-ethynyl-3,4-dihydro-1-(p-methoxybenzyl)quinazolin-2(1H)-one in 5 mL of CH2Cl2 was treated with 10 mL of trifluoroacetic acid (Aldrich) under N2 overnight at r.t. The reaction was concentrated by rotovap under reduced pressure and the residue partitioned between ethyl acetate and 10% citric acid. The organic layer was washed with water, brine, dried over MgSO4 and the solvents removed to give an oil which was flash chromatographed on SiO2 using 95:5 CHCl3 --CH3OH to give a foam. Trituration of this material with ether gave 720 mg (80%) of the title compound as a colorless solid.

Workup

  1. concentrationThe reaction was concentrated by rotovap under reduced pressure
  2. customthe residue partitioned between ethyl acetate and 10% citric acid
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over MgSO4
  5. customthe solvents removed
  6. customto give an oil which
  7. customchromatographed on SiO2 using 95:5 CHCl3
  8. customCH3OH to give a foam

Sources & evidence

ORD record
ord-219f890163c44f66b38a93da8d36d092
Source dataset
uspto-grants-1995_10
Patent number
US05457201

Reaction notes

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