Ethanolamine → 2-{4-[(3,4-Dimethoxy-phenyl)-methyl-amino]-quinazolin-2-ylamino}-ethanol

HRID 1876172Notes

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])=[C:17]([O:23][CH3:24])[CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH2:25]([CH2:27][NH2:28])[OH:26]>C(O)CCC>[CH3:24][O:23][C:17]1[CH:16]=[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]([NH:28][CH2:27][CH2:25][OH:26])[N:12]=2)[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of (2-chloro-quinazolin-4-yl)-(3,4-dimethoxy-phenyl)-methyl-amine hydrochloride (63 mg; 0.172 mmol) and ethanolamine (32 μL; 0.53 mmol) in n-butanol (2 mL) was heated at 110° C. for 24 h then concd in vacuo. The material was partitioned between DCM (5 mL) and satd NaHCO3 (3 mL). The organic layer was dried (MgSO4), filtered through silica and washed with 100:10:1 CHCl3:MeOH:concd NH4OH, concd then purified by pTLC (EM-13793; 100:10:1 CHCl3:MeOH:concd NH4OH) yielding a pale yellow glass (52 mg; 85%). 1H NMR (CDCl3) δ 7.44-7.34 (m, 2H), 6.88 (m, 1H), 6.84 (d, J=8.4 Hz, 1H), 6.75-6.67 (m, 3H), 5.42 (t(br), 1H), 3.91 (s, 3H), 3.91 (m, 2H), 3.79 (s, 3H), 3.68 (m, 2H), 3.50 (s, 3H); LC-MS (ESI+; 355 ([M+H]+).

Workup

customThe material was partitioned between DCM (5 mL) and satd NaHCO3 (3 mL)
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered through silica
washwashed with 100:10:1 CHCl3
customMeOH:concd NH4OH, concd then purified by pTLC (EM-13793; 100:10:1 CHCl3:MeOH:concd NH4OH)
customyielding a pale yellow glass (52 mg; 85%)

Sources & evidence

ORD record: ord-ab23632f18674bea8e36efaa1f262efc
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309562B2

Reaction notes

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