4-Chloro-2-(chloromethyl)quinazoline → HCID 59242024, compound

HRID 1876225Notes

Reaction equation

HRID 1876225 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[N:13]=[C:12]([N:14]([C:16]2[CH:21]=[C:20]([Cl:22])[C:19]([O:23][CH3:24])=[C:18]([Cl:25])[CH:17]=2)[CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.ClC1C2C(=CC=CC=2)N=C(CCl)N=1.Cl.ClC1C=C(NC)C=C(Cl)C=1OC>CC(O)C>[Cl:2][CH2:3][C:4]1[N:13]=[C:12]([N:14]([C:16]2[CH:17]=[C:18]([Cl:25])[C:19]([O:23][CH3:24])=[C:20]([Cl:22])[CH:21]=2)[CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

5

Reactant 3

HCID 131575204-Chloro-2-(chloromethyl)quinazolineHCID 68514553HCID 68514553, compoundHCID 68516808HCID 68516808, compound

Product 1

HCID 59242024HCID 59242024, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(2-Chloromethyl-quinazolin-4-yl)-(3,5-dichloro-4-methoxy-phenyl)-methyl-amine hydrochloride: A mixture of 4-chloro-2-chloromethyl-quinazoline (320 mg, 1.50 mmol) and (3,5-dichloro-4-methoxy-phenyl)-methyl-amine hydrochloride (401 mg, 1.65 mmol) in i-PrOH was stirred at rt for 2.8 h then collected by filtration and washed with i-PrOH, yielding the title compound as a light tan solid (529 mg; 84%). 1H NMR (CDCl3) δ 8.59 (m, 1H), 7.87 (m, 1H), 7.37 (m, 1H), 7.33 (s, 2H), 6.94 (m, 1H), 5.11 (s, 2H), 4.02 (s, 3H), 3.85 (s, 3H), LC-MS (ESI+; 382 ([M+H]+)).

Workup

  1. filtrationthen collected by filtration
  2. washwashed with i-PrOH

Sources & evidence

ORD record
ord-b0b1498f3a614a68a57c3e1728b5e221
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

Loading…