Triethylamine → HCID 19605759, compound

HRID 1603540Notes

Reaction equation

HRID 1603540 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2OC.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[C:24]#[CH:25].[CH2:26](N(CC)CC)[CH3:27]>CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[C:24]#[C:25][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[CH2:26][CH3:27]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 110949512,5-DimethoxyphenylacetyleneHCID 196057826-Iodo-4-methoxyquinazoline

Product 1

HCID 19605759HCID 19605759, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Argon is passed through a solution of 200 mg of 6-iodo-4-methoxy-quinazoline in 12 ml of dry dimethylformamide for 15 minutes. Then 40 mg of tetrakis(triphenylphosphine)-palladium, 113 mg of (2,5-dimethoxyphenyl)acetylene, 11 mg of copper(I)iodide and 220 mg of triethylamine are added, and the mixture is heated to 60° for 2 hours. The solvent is distilled off in vacuo and the residue partitioned between water and ethyl acetate. The organic layer is separated, dried and concentrated in vacuo. The pure title compound is obtained after chromatography (silica gel, cyclohexane/ethyl acetate=2/1) as colourless crystals. mp: 103-105°.

Workup

  1. temperaturethe mixture is heated to 60° for 2 hours
  2. distillationThe solvent is distilled off in vacuo
  3. customthe residue partitioned between water and ethyl acetate
  4. customThe organic layer is separated
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c72c183a37848fbae9abcc2e483b0ac
Source dataset
uspto-grants-1999_11
Patent number
US05990116

Reaction notes

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