4-Chloro-6-iodoquinazoline → (6-Iodo-quinazolin-4-yl)-[3-methyl-4-(6-methyl-pyridin-3-yloxy)-phenyl]-amine

HRID 877096Notes

Reaction equation

HRID 877096 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=2[CH3:16])=[CH:4][CH:3]=1.Cl[C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([I:28])[CH:26]=2)[N:21]=[CH:20][N:19]=1>C(O)(C)C>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([I:28])[CH:26]=4)[N:21]=[CH:20][N:19]=3)=[CH:11][C:10]=2[CH3:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 111738094-Chloro-6-iodoquinazolineHCID 114244343-Methyl-4-((6-methylpyridin-3-yl)oxy)aniline

Product 1

HCID 11282772(6-Iodo-quinazolin-4-yl)-[3-methyl-4-(6-methyl-pyridin-3-yloxy)-phenyl]-amineYield 69.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-(6-methylpyridin-3-yloxy)-3-methylbenzenamine (812 mg, 3.79 mmol) and 4-chloro-6-iodo-quinazoline (1 g, 3.4 mmol) were dissolved in isopropanol (50 ml). The reaction mixture was refluxed for 12 hours. The solid product was collected by filtration, washed with cold isopropanol (10 mL) and ether (20 mL), and air dried to afford 1.1 g of the clean desired material.

Workup

  1. temperatureThe reaction mixture was refluxed for 12 hours
  2. filtrationThe solid product was collected by filtration
  3. washwashed with cold isopropanol (10 mL) and ether (20 mL), and air
  4. customdried

Sources & evidence

ORD record
ord-53eb5107be0646dda17bb3c6a7b3c760
Source dataset
uspto-grants-2015_03
Patent number
US08987284B2

Reaction notes

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