O-Xylene → 5-Allyl-4-(4-bromo-2-fluoro-phenylamino)-7-methoxy-quinazolin-6-ol

HRID 1351216Notes

Reaction equation

HRID 1351216 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]([Br:24])=[CH:20][C:19]=1[F:25])C=C.[CH3:26][C:27]1C=CC=C[C:32]=1C>>[CH2:32]([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][C:21]([Br:24])=[CH:20][C:19]=1[F:25])=[N:9][CH:10]=[N:11]2)[CH:27]=[CH2:26]

Participants

3

Reactant 2

HCID 7237O-XyleneHCID 21098402(6-Allyloxy-7-methoxy-quinazolin4-yl)-(4-bromo-2-fluoro-phenyl)-amine

Product 1

HCID 112811415-Allyl-4-(4-bromo-2-fluoro-phenylamino)-7-methoxy-quinazolin-6-ol

Procedure

A solution of (6-allyloxy-7-methoxy-quinazolin-4-yl)-(4-bromo-2-fluoro-phenyl)-amine (0.46 g, 1.13 mmol) (from Example 19, Step C, supra) in o-xylene (75 mL) was heated at 150° C. for 4 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 solution was concentrated to a small volume and filtered. The solid was collected and dried in vacuo to give the desired 5-allyl-4-(4-bromo-2-fluoro-phenylamino)-7-methoxy-quinazolin-6-ol as an off white solid. (Yield 0.35 g, 76%).

Workup

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

Sources & evidence

ORD record
ord-caeb5197e15642dba4046d79bbbfd3a5
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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