n-Methyl-p-aminophenol → (2-Chloromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine

HRID 1876207Notes

Reaction equation

HRID 1876207 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[N:13]=[C:12]([N:14]([CH3:22])[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.Cl[C:24]1C2C(=CC=CC=2)N=C(CCl)N=1.CNC1C=CC(O)=CC=1>C(O)(C)C.Cl>[Cl:2][CH2:3][C:4]1[N:13]=[C:12]([N:14]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:24])=[CH:19][CH:20]=2)[CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

6

Reactant 3

HCID 5931n-Methyl-p-aminophenolHCID 131575204-Chloro-2-(chloromethyl)quinazolineHCID 68513966HCID 68513966, compound

Product 1

HCID 11358914(2-Chloromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent

Procedure

4-[(2-Chloromethyl-quinazolin-4-yl)-methyl-amino]-phenol hydrochloride: To 4-chloro-2-chloromethyl-quinazoline (200 mg) suspended in isopropanol (3 ml) was added 4-methylamino-phenol (389 mg) and followed by HCl (12 M, 2 drops). The reaction was stirred overnight at room temperature. The resulting precipitate was filtered to give 391 mg of (2-chloromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine as the hydrochloride salt. 1H NMR (MeOH-d4) δ 7.28 (m, 4H), 6.90 (m, 4H), 4.8 (s, 2H), 3.8 (s, 3H); LC-MS (ESI+; 332 ([M+H]+)).

Workup

  1. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-e8bdd495293b4c09a90b1651217353b3
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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