2-Chloro-6,7-dimethoxy-4-quinazolinamine → HCID 9893021, compound

HRID 1274131Notes

Reaction equation

HRID 1274131 reaction equation
[NH2:1][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]=[C:4](Cl)[N:3]=1.[C:17]([O:21][C:22](=[O:39])[C:23]1[CH:28]=[CH:27][C:26]([NH:29][CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[C:25]([N+:36]([O-:38])=[O:37])[CH:24]=1)([CH3:20])([CH3:19])[CH3:18]>C(O)CCCC>[C:17]([O:21][C:22](=[O:39])[C:23]1[CH:28]=[CH:27][C:26]([NH:29][CH:30]2[CH2:35][CH2:34][N:33]([C:4]3[N:3]=[C:2]([NH2:1])[C:11]4[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=3)[CH2:32][CH2:31]2)=[C:25]([N+:36]([O-:38])=[O:37])[CH:24]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 10710909HCID 10710909, compound

Product 1

HCID 9893021HCID 9893021, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Conditions

Temperature
120 °C

Procedure

4-Amino-2-chloro-6,7-dimethoxyquinazoline (0.08 g, 0.33 mmol) was added to a solution of (44) (0.11 g, 0.35 mmol) in n-pentanol (5 mL) at 25° C. The mixture was heated to 120° C. and maintained at that temperature for 12 h. The reaction mixture was then cooled to room temperature and the desired product was filtered and rinsed with acetone to give 0.11 g (64%) of the title compound: TLC (Rf =0.30; 5% MeOH/CH2Cl2); 1H NMR (DMSO) δ 12.23 (s, 1H), 8.89 (s, 1H), 8.65 (s, 1H), 8.56 (s, 1H, J=2.0), 8.23 (d, 1H, J=7.8), 7.94 (d, 1H, J=9.2), 7.74 (s, 1H), 7.55 (s, 1H), 7.34 (d, 1H, J=9.3), 4.62 (d, 2H, J=13.3), 4.15 (m, 1H), 3.87 (s, 3H), 3.84 (s, 3H), 3.35 (t, 2H, J=11.6), 2.10 (d, 2H, J=11.3), 1.74 (m, 2H), 1.53 (s, 9H); 13C NMR (DMSO) δ 163.5, 161.4, 155.2, 151.2, 146.8, 146.2, 136.3, 135.8, 130.6, 128.2, 117.9, 115.1, 104.9, 101.6, 99.1, 80.8, 56.2, 56.0, 48.8, 43.5, 30.5, 27.8; HRMS (FAB) m/z 525.2456 (M+H)+ (C26H32N6O6 requires 525.2454); Anal. (C26H32N6O6 ·1HCl) C, H, N.

Workup

  1. temperaturemaintained at that temperature for 12 h
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. filtrationthe desired product was filtered
  4. washrinsed with acetone

Sources & evidence

ORD record
ord-5810ee499c0d436891a043fd99698f68
Source dataset
uspto-grants-2000_12
Patent number
US06156758

Reaction notes

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