Phenol → 6-Cyclobutyl-N-(4-phenoxyphenyl)-4-quinazolinamine

HRID 1264052Notes

Reaction equation

HRID 1264052 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[N:3][CH:2]=1.[O:11]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:25]1(O)[CH:30]=[CH:29][CH:28]=CC=1>>[CH:28]1([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:1]=[CH:2][N:3]=[C:4]3[NH:22][C:21]2[CH:20]=[CH:19][C:18]([O:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:24][CH:23]=2)[CH2:29][CH2:30][CH2:25]1

Participants

4

Reactant 3

HCID 996PhenolHCID 8764(4-Aminophenoxy)benzeneHCID 9210Quinazoline

Product 1

HCID 186163756-Cyclobutyl-N-(4-phenoxyphenyl)-4-quinazolinamineYield 30.2%

Conditions

Temperature
100 °C

Procedure

Quinazoline 16 (50 mg, 0.18 mmol) was combined with 4-phenoxyaniline (67 mg, 0.36 mmol) in phenol (0.45 g). The mixture was heated at 100° C. for a total of 17 hours. Excess phenol was removed by distillation under reduced pressure to provide a residue which was triturated with CH2Cl2 to provide the desired quinazoline 17 (20 mg, 30%) as a yellow solid. 1H NMR (DMSO d6, 400 MHz): δ: 9.76 (s, 1H), 8.47 (s, 1H), 8.31 (s, 1H), 7.77 (d, 2H), 7.69 (m, 2H), 7.36 (t, 2H), 7.11 (t, 1H), 7.03 (d, 2H), 6.98 (d, 2H), 3.69 (m, 1H), 2.35 (m, 2H), 2.23 (m, 2H), 2.01 (m, 1H), 1.86 (m, 1H).

Workup

  1. customExcess phenol was removed by distillation under reduced pressure
  2. customto provide a residue which
  3. customwas triturated with CH2Cl2

Sources & evidence

ORD record
ord-5228f8fce245441db07459772150d2ad
Source dataset
uspto-grants-2003_04
Patent number
US06541481B2

Reaction notes

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