2-(Methylamino)ethanol → 2-({4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-yl}-methyl-amino)-ethanol

HRID 1876173Notes

Reaction equation

HRID 1876173 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]=[CH:7][CH:8]=2)[N:3]=1.[CH3:22][NH:23][CH2:24][CH2:25][OH:26]>>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([N:12]([CH3:13])[C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([N:23]([CH3:22])[CH2:24][CH2:25][OH:26])[N:11]=2)=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 117381122-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine

Product 1

HCID 592421272-({4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-yl}-methyl-amino)-ethanol

Conditions

Temperature
130 °C

Procedure

A mixture of (2-chloroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine 0.335 g (1.0 mmol), 2-methylamino-ethanol 1.0 mL was stirred at 130° C. for 20 minutes under microwave irradiation. The crude mixture was directly charged to silica-gel, and purified by MPLC (SiO2, EtOAc 0˜100% in hexanes) to give the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.31-7.40 (m, 2H), 7.08-7.11 (m, 2H), 6.87-6.90 (m, 2H), 6.81-6.84 (m, 1H), 6.61-6.65 (m, 1H), 3.94-3.96 (m, 2H), 3.84-3.86 (m, 2H), 3.82 (s, 3H), 3.51 (s, 3H), 3.34 (s, 3H); HRMS (ES) m/z calcd for C19H22N4O2 (M+H) 339.1815, found 339.1830.

Workup

  1. custompurified by MPLC (SiO2, EtOAc 0˜100% in hexanes)

Sources & evidence

ORD record
ord-e2c6cbd1ef884a1f8005f8eea983c79b
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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