N,N'-Dimethylethylenediamine → N4-(4-Methoxy-phenyl)-N2,N4-dimethyl-N2-(2-methylamino-ethyl)-quinazoline-2,4-diamine

HRID 1876149Notes

Reaction equation

HRID 1876149 reaction equation
Cl.Cl[C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH3:23][NH:24][CH2:25][CH2:26][NH:27][CH3:28]>C(O)CCC>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([N:13]([CH3:14])[C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=[C:3]([N:24]([CH3:23])[CH2:25][CH2:26][NH:27][CH3:28])[N:12]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 8070N,N'-DimethylethylenediamineHCID 86639964(2-Chloroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine hydrochloride

Product 1

HCID 59242059N4-(4-Methoxy-phenyl)-N2,N4-dimethyl-N2-(2-methylamino-ethyl)-quinazoline-2,4-diamineYield 80%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of (2-chloroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine hydrochloride (120 mg, 0.36 mmol) and N,N′-dimethylethylenediamine (0.14 mL, 1.26 mmol) in 2 mL of 1-butanol was heated at 100° C. overnight with stirring. The mixture was concentrated and purified by silica gel column chromatography to give the title compound (101 mg, 80%). 1H NMR (CDCl3, 400 MHz) δ 7.42 (d, 1H, J=8.4 Hz), 7.31 (t, 1H, J=6.8 Hz), 7.09 (d, 2H, J=8.8 Hz), 6.86 (m, 3H), 6.64 (t, 1H, J=6.8 Hz), 3.90 (t, 2H, J=6.4 Hz), 3.82 (s, 3H), 3.50 (s, 3H), 3.30 (s, 3H), 2.92 (t, 2H, J=6.4 Hz), 2.50 (s, 3H); ESI-MS m/z 352 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-3189715498a142e59f79c7a98aae05fd
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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