2-Chloro-6,7-dimethoxy-4-quinazolinamine → HCID 9932846, compound

HRID 1274128Notes

Reaction equation

HRID 1274128 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[N:6][CH:5]=1.[NH2:18][C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[C:21](Cl)[N:20]=1>C(O)CC(C)C>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([C:21]3[N:20]=[C:19]([NH2:18])[C:28]4[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=4)[N:22]=3)[CH2:13][CH2:12]2)=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 10752245HCID 10752245, compound

Product 1

HCID 9932846HCID 9932846, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

Compound (40) (1.18 g, 5 mmol) was added to a solution of 4-amino-2-chloro-6,7-dimethoxyquinazoline (1.0 g, 4 mmol) in isoamyl alcohol (10 mL) at 25° C. The mixture was stirred at 120 C. for 12 h. The reaction mixture was then cooled to room temperature and the desired product was filtered and rinsed with acetone to give 1.5 g (68%) of the title compound; 1H NMR (DMSO) δ 12.37 (s, 1H), 8.74 (d, 2H, J=6.3), 8.57 (d, 1H, J=2.2), 7.80 (m, 1H), 7.76 (s, 1H), 7.62 (s, 1H), 7.60 (d, 1H, J=8.8), 6.56 (d, 1H, J=8.9), 4.57 (m, 2H), 4.20 (m, 1H), 3.86 (s, 3H), 3.84 (s, 3H), 3.76 (s, 3H), 3.42 (m, 2H), 2.03 (m, 2H), 1.51 (m, 2H); 13C NMR (DMSO) δ 165.6, 161.3, 160.2, 155.1, 151.0, 150.6, 146.6, 136.8, 136.4, 113.1, 107.9, 105.2, 101.5, 99.3, 56.2, 55.9, 51.2, 46.6, 43.4, 30.9; HRMS (FAB) m/z 439.2083 (M+H)+ (C22H26N6O4 requires 439.2094); Anal. (C22H26N6O4 ·1HCl) C, H, N.

Workup

  1. filtrationthe desired product was filtered
  2. washrinsed with acetone

Sources & evidence

ORD record
ord-3b8e69f7908d454aa445b6bd9b0d0044
Source dataset
uspto-grants-2000_12
Patent number
US06156758

Reaction notes

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