Triethylamine → N2-(2-amino-ethyl)-N4-(4-methoxy-phenyl)-N4-methyl-quinazoline-2,4-diamine

HRID 1876148Notes

Reaction equation

HRID 1876148 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][NH:10][C:11]1[N:20]=[C:19]([N:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[CH3:22])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1)(C)(C)C.ClC1N=C(N(C2C=CC(OC)=CC=2)C)C2C(=CC=CC=2)N=1.C(OC(=O)NCCN)(C)(C)C.CCN(CC)CC>C(O)(C)C.C(Cl)Cl.CO.C(Cl)Cl>[NH2:7][CH2:8][CH2:9][NH:10][C:11]1[N:20]=[C:19]([N:21]([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[CH3:22])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 117381122-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amineHCID 59237304(2-{4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-ylamino}-ethyl)-carbamic acid tert-butyl ester

Product 1

HCID 59242058N2-(2-amino-ethyl)-N4-(4-methoxy-phenyl)-N4-methyl-quinazoline-2,4-diamine

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
85 °C

Procedure

(2-{4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-ylamino}-ethyl)-carbamic acid tert-butyl ester: A mixture of (2-chloro-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine 1.50 g (4.47 mmol) and (2-amino-ethyl)-carbamic acid tert-butyl ester 0.94 g (5.60 mmol) with Et3N 2 mL in isopropanol was stirred at 85° C. for 48 h. The reaction mixture was diluted with CH2Cl2 and directly charged to gradient column chromatography (MeOH/CH2Cl2, 0% to 10%) to obtain the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.44 (d, 1H, J=8.2 Hz), 7.40-7.36 (m, 1H), 7.11 (d, 2H, J=9.0 Hz), 6.91 (d, 2H, J=9.0 Hz), 6.85 (d, 1H, J=8.6 Hz), 6.72-6.67 (m, 1H), 3.84 (s, 3H), 3.68 (q, 2H, J=5.4 Hz), 3.52 (s, 3H), 3.43 (q, 2H, J=5.4 Hz), 1.43 (s, 9H); LC-MS (ESI+; 424 ([M+H]+)).

Sources & evidence

ORD record
ord-40f31a6e02b1480ab511105fe742aff9
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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