4-Chloro-2-(chloromethyl)quinazoline → HCID 59242112, compound

HRID 1876199Notes

Reaction equation

HRID 1876199 reaction equation
Cl[CH2:2][C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:22]([CH3:24])[CH3:23])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.ClC1C2C(=CC=CC=2)N=C(CCl)[N:27]=1.C(OC1C=CC(NC)=CC=1)(C)C>Cl>[NH2:27][CH2:2][C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:22]([CH3:24])[CH3:23])=[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 3

HCID 131575204-Chloro-2-(chloromethyl)quinazolineHCID 18002910N-Methyl-4-[(propan-2-yl)oxy]anilineHCID 68518575HCID 68518575, compound

Product 1

HCID 59242112HCID 59242112, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

(2-Chloromethyl-quinazolin-4-yl)-(4-isopropoxy-phenyl)-methyl-amine: The title compound was prepared from 4-chloro-2-chloromethyl-quinazoline (300 mg, 1.4 mmol), 4-isopropoxy-N-methylaniline (279 mg, 1.7 mmol) and concd HCl (12 M, 10 drops) by a procedure similar to Example 203c with subsequent MPLC purification. 1H NMR (CDCl3) δ 7.8 (d, 1H), 7.55 (m, 1H), 7.10 (d, 2H), 7.0 (m, 2H), 6.9 (d, 2H), 4.7 (s, 2H), 4.5 (sept, 1H), 3.6 (s, 3H), 1.37 (d, 6H); LC-MS (ESI+; 342 ([M+H]+)).

Sources & evidence

ORD record
ord-a25f271e95d2467b89c1504ab2e54267
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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