1,2-Dichloroethane → 4-Quinazolinamine,6-iodo-n-[3-methyl-4-[(6-methyl-3-pyridinyl)oxy]phenyl]-,hydrochloride

HRID 415004Notes

Reaction equation

HRID 415004 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:16])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1.[Cl:17][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.ClCCCl>CC(O)(C)C>[ClH:17].[I:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][N:19]=[C:18]2[NH:16][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[C:2]([CH3:1])[CH:3]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 111738094-Chloro-6-iodoquinazolineHCID 114244343-Methyl-4-((6-methylpyridin-3-yl)oxy)aniline

Product 1

HCID 666233074-Quinazolinamine,6-iodo-n-[3-methyl-4-[(6-methyl-3-pyridinyl)oxy]phenyl]-,hydrochlorideYield 76%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-methyl-4-(6-methyl-pyridin-3-yloxy)-phenylamine (4.96 g, 23.18 mmol), 4-Chloro-6-iodo-quinazoline 604 g, 22.06 mmol) in tBuOH (60 mL) and DCE (60 mL) was refluxed for 6 hours. The reaction was cooled to 0° C. and the solid product (8.44 g, 76%) was isolated by filtration and washed with cold CH2Cl2 (50 mL).

Sources & evidence

ORD record
ord-9892228857a047a982fb3083ebe4fefa
Source dataset
uspto-grants-2012_01
Patent number
US08088766B2

Reaction notes

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