4-Aminopyridine → HCID 86703930, compound

HRID 1049932Notes

Reaction equation

HRID 1049932 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[N:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1>Cl.O1CCOCC1.ClCCl>[I:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][N:3]=[C:2]2[NH:19][C:16]1[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 17274-AminopyridineHCID 111738094-Chloro-6-iodoquinazoline

Product 1

HCID 86703930HCID 86703930, compound

Reagents, catalysts & solvents 2

HCID 204431481,4-Dioxane hydrochlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a vial was added 4-chloro-6-iodo-quinazoline (100 mg; 0.34 mmol, commercially available), pyridin-4-amine (3 equiv., 1.03 mmol, 97.19 mg, commercially available), and 2 drops of 4M HCl/dioxane. The reaction vial was heated until solids melted. LCMS of resultant solution showed clean product formation. Upon cooling the product re-solidified. The solid was suspended in dichloromethane:water, and collected by filtration. 95 mg of 6-iodo-N-(4-pyridyl)quinazolin-4-amine was recovered as an orange solid, which was carried on directly to the Suzuki step. LCMS M/Z (M+H)=350.

Workup

  1. customThe reaction
  2. temperaturevial was heated until solids
  3. temperatureUpon cooling the product re-solidified
  4. filtrationwater, and collected by filtration
  5. custom95 mg of 6-iodo-N-(4-pyridyl)quinazolin-4-amine was recovered as an orange solid, which

Sources & evidence

ORD record
ord-93781137f8ed4d6f968ad919adb14fcf
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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