O-Xylene → 5-Allyl-4-(3-bromo-phenylamino)-7-methoxy-quinazolin-6-ol

HRID 1351205Notes

Reaction equation

HRID 1351205 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][CH:21]=[C:20]([Br:24])[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:23]=[CH:22][CH:21]=[C:20]([Br:24])[CH:19]=1)=[N:9][CH:10]=[N:11]2)[CH:26]=[CH2:25]

Participants

3

Reactant 2

HCID 7237O-XyleneHCID 21098400(6-Allyloxy-7-methoxy-quinazolin-4-yl)-(3-bromo-phenyl)-amine

Product 1

HCID 112691685-Allyl-4-(3-bromo-phenylamino)-7-methoxy-quinazolin-6-ol

Procedure

A solution of (6-allyloxy-7-methoxy-quinazolin-4-yl)-(3-bromo-phenyl)-amine (0.54 g, 1.39 mmol) (from Example 17, Step C, supra) in o-xylene (75 mL) was heated at 150° C. for 4.5 hours, during which time TLC analysis indicated almost complete consumption of the starting material and the formation of desired product as the major spot. The solution was concentrated and filtered. The solid was collected and dried in vacuo to give the desired 5-allyl-4-(3-bromo-phenylamino)-7-methoxy-quinazolin-6-ol as an off white solid. (Yield 0.33 g, 61%).

Workup

  1. customconsumption of the starting material
  2. concentrationThe solution was concentrated
  3. filtrationfiltered
  4. customThe solid was collected
  5. customdried in vacuo

Sources & evidence

ORD record
ord-804443d7e37d4a0da1d83f566fa2395e
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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