O-Xylene → HCID 11439274, compound

HRID 1351198Notes

Reaction equation

HRID 1351198 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][N:9]=[C:8]2[NH:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)C=C.[CH3:25][C:26]1C=CC=C[C:31]=1C>>[CH2:31]([C:6]1[C:5]([OH:4])=[C:14]([O:15][CH3:16])[CH:13]=[C:12]2[C:7]=1[C:8]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)=[N:9][CH:10]=[N:11]2)[CH:26]=[CH2:25]

Participants

3

Reactant 2

HCID 7237O-XyleneHCID 21098403(6-Allyloxy-7-methoxy-quinazolin-4-yl)-(4-chloro-phenyl)-amine

Product 1

HCID 11439274HCID 11439274, compound

Procedure

A solution of (6-allyloxy-7-methoxy-quinazolin-4-yl)-(4-chloro-phenyl)-amine (0.50 g, 1.46 mmol) (from Example 16, Step C, supra) in o-xylene (50 mL) was heated at 150° C. for 7 hours. At the end of this period, TLC analysis indicated almost complete consumption of the starting material and the formation of desired product as the major spot. The solvent was evaporated and the residue was purified by chromatography using EtOAc/Et3N (1:0.04) as eluent to give the desired 5-allyl-4-(4-chloro-phenylamino)-7-methoxy-quinazolin-6-ol as an off white solid. (Yield 0.4 g, 80%).

Workup

  1. customconsumption of the starting material
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-779ade81932e41a2aeb395557143ff52
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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