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

HRID 1351210Notes

Reaction equation

HRID 1351210 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]([F:24])=[C:20]([Cl:25])[CH:19]=1)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]([F:24])=[C:20]([Cl:25])[CH:19]=1)=[N:9][CH:10]=[N:11]2)[CH:27]=[CH2:26]

Participants

3

Reactant 2

HCID 7237O-XyleneHCID 21098401(6-Allyloxy-7-methoxy-quinazolin-4-yl)-(3-chloro-4-fluoro-phenyl)-amine

Product 1

HCID 114625295-Allyl-4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-quinazolin-6-ol

Procedure

A solution of (6-allyloxy-7-methoxy-quinazolin-4-yl)-(3-chloro-4-fluoro-phenyl)-amine (0.92 g, 2.55 mmol) (from Example 18, Step C, supra) in o-xylene (150 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 solution was concentrated and filtered. The solid was collected and dried in vacuo to give the desired 5-allyl-4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-quinazolin-6-ol as an off white solid. (Yield 0.65 g, 71%).

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-09ea2d8b417a48c78b48bc0f6ef45f3b
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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