tert-Butanol → [3-Chloro-4-(3-fluorobenzyloxy)phenyl](6-iodoquinazolin-4-yl)amine hydrochloride

HRID 415000Notes

Reaction equation

HRID 415000 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:17])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.Cl[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([I:29])[CH:27]=2)[N:22]=[CH:21][N:20]=1.CC(O)(C)C>ClCCCl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([I:29])[CH:27]=3)[N:22]=[CH:21][N:20]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineHCID 111738094-Chloro-6-iodoquinazoline

Product 1

HCID 66623345[3-Chloro-4-(3-fluorobenzyloxy)phenyl](6-iodoquinazolin-4-yl)amine hydrochlorideYield 116.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-Chloro-4-(3-fluoro-benzyloxy)-phenylamine (3.1 g, 12 mmol) and 4-chloro-6-iodo-quinazoline (3.28 g, 11.3 mmol) are dissolved in a 1:1 mixture of DCE:t-BuOH (56 ml). The reaction mixture is refluxed for 19 hours. The product is isolated by suction filtration through sintered glass, washed with excess DCM, and air dried to afford 3.8 g (7.0 mmol, 58%) of the clean desired material.

Workup

  1. temperatureThe reaction mixture is refluxed for 19 hours
  2. customThe product is isolated by suction filtration through sintered glass
  3. washwashed with excess DCM, and air
  4. customdried

Sources & evidence

ORD record
ord-b1d8e342edf4422ba3f0e569c4382ad2
Source dataset
uspto-grants-2012_01
Patent number
US08088766B2

Reaction notes

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