2-(Dimethylamino)ethanol → [2-(2-Dimethylamino-ethoxy)-quinazolin-4-yl]-(4-methoxy-phenyl)-methyl-amine

HRID 1876150Notes

Reaction equation

HRID 1876150 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.CC(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1.[CH3:47][N:48]([CH3:52])[CH2:49][CH2:50][OH:51]>>[CH3:47][N:48]([CH3:52])[CH2:49][CH2:50][O:51][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

Participants

5

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 2855718-Crown-6HCID 23665647Potassium tert-butoxideHCID 86639964(2-Chloroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine hydrochloride

Product 1

HCID 59242106[2-(2-Dimethylamino-ethoxy)-quinazolin-4-yl]-(4-methoxy-phenyl)-methyl-amineYield 52%

Conditions

Temperature
100 °C

Procedure

To a solution of (2-chloroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine hydrochloride (120 mg, 0.36 mmol) in 2 mL of N,N-dimethylethanolamine were added potassium tert-butoxide (121 mg, 1.07 mmol) and 18-crown-6 (95 mg, 0.36 mmol). The resulting solution was heated at 100° C. overnight with stirring. The mixture was concentrated and purified by silica gel column chromatography to give the title compound (66 mg, 52%). 1H NMR (CDCl3, 400 MHz) δ 7.59 (d, 1H, J=8.4 Hz), 7.45 (t, 1H, J=6.8 Hz), 7.10 (d, 2H, J=8.8 Hz), 6.92 (m, 3H), 6.83 (t, 1H, J=6.8 Hz), 4.60 (t, 2H, J=6.4 Hz), 3.83 (s, 3H), 3.57 (s, 3H), 2.84 (t, 2H, J=6.4 Hz), 2.38 (s, 6H); ESI-MS m/z 353 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-e87a27fc443a42a7bcf78fbb36de03a6
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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