Dimethylamine → (2-Dimethylamino-6-nitroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine

HRID 1668782Notes

Reaction equation

HRID 1668782 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:22]([O-:24])=[O:23])[CH:8]=2)[N:3]=1.CO.[CH3:27][NH:28][CH3:29]>>[CH3:27][N:28]([CH3:29])[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:22]([O-:24])=[O:23])[CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 887MethanolHCID 11609884(2-Chloro-6-nitroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine

Product 1

HCID 11501245(2-Dimethylamino-6-nitroquinazolin-4-yl)-(4-methoxyphenyl)-methylamineYield 79%

Procedure

A solution of (2-chloro-6-nitroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine (48 mg, 0.14 mmol) in 2 mL of dimethylamine in methanol (2M, 25 mmol) was heated overnight in a seal tube at 70° C. for 48 h. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was purified by chromatography (15% ethyl acetate/hexane) to give the title compound (39 mg, 79%). 1H NMR (CDCl3): 8.08 (dd, J=9.3, 2.4, 1H), 7.71 (d, J=2.4, 1H), 7.35 (d, J=9.3, 1H), 7.14 (m, 2H), 6.97 (2H), 3.85 (s, 3H), 3.55 (s, 3H), 3.33 (s, 6H).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by chromatography (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b02728f8afd64fd8bc57cab8e1cb9a30
Source dataset
uspto-grants-2011_08
Patent number
US07989462B2

Reaction notes

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