2,4-Dichloroquinazoline → N4-(3,4-Dimethoxy-phenyl)-N2,N4-dimethyl-quinazoline-2,4-diamine

HRID 1876166Notes

Reaction equation

HRID 1876166 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.Cl[C:26]1N=C(Cl)C2C(=CC=CC=2)[N:27]=1.COC1C=C(NC)C=CC=1OC>Cl.CC(O)C>[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:27][CH3:26])[N:12]=2)[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]

Participants

6

Reactant 3

HCID 2528862,4-DichloroquinazolineHCID 27869553,4-dimethoxy-N-methylanilineHCID 86639965(2-Chloro-quinazolin-4-yl)-(3,4-dimethoxy-phenyl)-methyl-amine hydrochloride

Product 1

HCID 59242114N4-(3,4-Dimethoxy-phenyl)-N2,N4-dimethyl-quinazoline-2,4-diamine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent

Procedure

(2-Chloro-quinazolin-4-yl)-(3,4-dimethoxy-phenyl)-methyl-amine hydrochloride: A mixture of 2,4-dichloro-quinazoline (88 wt %, 758 mg, 3.4 mmol), (3,4-dimethoxy-phenyl)-methyl-amine (502 mg, 3.00 mmol) and 2 drops of concd HCl in i-PrOH (11 mL) was reacted for 16 h then the product was collected on a Büchner funnel, washed with i-PrOH and dried. The title compound was obtained as a pale yellow solid (792 mg; 72%). 1H NMR (CDCl3) δ 8.65 (m, 1H), 7.75 (m, 1H), 7.18 (m, 1H), 7.00 (d, J=8.4 Hz, 1H), 6.90 (m, 1H), 6.85-6.78 (m, 2H), 3.99 (s, 3H), 3.87 (s, 3H), 3.83 (s, 3H); LC-MS (ESI+; 330 ([M+H]+)).

Workup

  1. customwas reacted for 16 h
  2. customthe product was collected on a Büchner funnel
  3. washwashed with i-PrOH
  4. customdried

Sources & evidence

ORD record
ord-78a9a61f3e24489c9b9a25f65f3d2142
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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