Carbon Tetrachloride → (6,7-Diethoxy-quinazolin-4-yl)-(3-ethynyl-phenyl)-amine Hydrochloride

HRID 1869092Notes

Reaction equation

HRID 1869092 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH2:15][CH3:16])[N:10]=[CH:9][NH:8][C:7]2=O)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:38].[C:42]([C:44]1[CH:45]=[C:46]([CH:48]=[CH:49][CH:50]=1)[NH2:47])#[CH:43]>C(O)(C)C>[ClH:38].[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH2:15][CH3:16])[N:10]=[CH:9][N:8]=[C:7]2[NH:47][C:46]1[CH:48]=[CH:49][CH:50]=[C:44]([C:42]#[CH:43])[CH:45]=1)[CH3:2]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 104682Benzenamine, 3-ethynyl-HCID 1354614006,7-diethoxyquinazolin-4(3H)-one

Product 1

HCID 18925066(6,7-Diethoxy-quinazolin-4-yl)-(3-ethynyl-phenyl)-amine Hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

6,7-Diethoxyquinazolin-4-one (120 mg, 0.512 mmol), triphenylphosphine (295 mg, 1.126 mmol) and 3 mL of carbon tetrachloride were refluxed for 16 hours. The reaction mixture was concentrated in vacuo to a residue which was diluted with 3 mL of isopropyl alcohol and 3-ethynylaniline (66 mg, 0.563 mmol) and refluxed for 3 hours. The cooled reaction mixture was filtered to afford solid title product which was washed with 10 mL of isopropyl alcohol and dried in vacuo at 70° C., 140 mg (75%); mp 269°-270° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to a residue which
  2. temperaturerefluxed for 3 hours
  3. customThe cooled reaction mixture
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-f0b031eb3652446ab52ce188754ecf8c
Source dataset
uspto-grants-2009_12
Patent number
USRE041065E1

Reaction notes

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