Triethylamine → 4-(3'-Bromo-4'-hydroxylphenyl)-amino-6,7-dimethoxy-quinazoline

HRID 392180Notes

Reaction equation

HRID 392180 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Br:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[OH:24])N.C([N:27](CC)CC)C>>[Br:16][C:17]1[CH:18]=[C:19]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[C:4]([NH2:27])[N:3]=2)[CH:21]=[CH:22][C:23]=1[OH:24]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 144402654-Amino-2-bromophenol

Product 1

HCID 1360489184-(3'-Bromo-4'-hydroxylphenyl)-amino-6,7-dimethoxy-quinazoline

Procedure

A mixture of 448 mg (2 mmol) of 4-chloro-6,7-dimethoxy-quioazoline (7) and 2.5 mmol of 3-bromo-4-hydroxyaniline in 20 ml of alcohol (EtOH or MeOH) was refluxed for 8 hours. After cooling, triethylamine was added to basify the solution, and the solvent was concentrated to give material that was recrystallized from DMF to give compound (2); 89.90%; m.p. 233.0-233.5° C.; 1H NMR(DMSO-d6): δ 10.08(s, 1H, —NH), 9.38(s, 1H, —OH), 8.40(s, 1H, 2-H), 7.89(d, 1H, J2′,5′=2.7 Hz, 2′-H), 7.75(s, 1H, 5-H), 7.55(dd, 1 H, J5′,6′=9.0 Hz, J2′,6′=2.7 Hz, 6′-H), 7.14(s, 1H, 8-H), 6.97(d, 1H, J5′,6′=9.0 Hz, 5′-H), 3.92(s, 3H, —OCHER), 3.90(s, 3H, —OCH3). UV(MeOH)λmax(e): 203.0, 222.0, 250.0, 335.0 nm. IR(KBr)umax: 3431(br), 2841, 1624, 1498, 1423, 1244 cm−1. GC/MS m/z 378( M+ +2, 90.68), 377(M+ +1,37.49), 376(M+, 100.00), 360(M+3.63), 298(18.86), 282 (6.65).

Workup

  1. temperaturewas refluxed for 8 hours
  2. temperatureAfter cooling
  3. concentrationthe solvent was concentrated
  4. customto give material that
  5. customwas recrystallized from DMF

Sources & evidence

ORD record
ord-255e3ec0230746f09c1df32c4d992fc0
Source dataset
uspto-grants-2004_10
Patent number
US06800649B1

Reaction notes

Loading…