3,4-dimethoxy-N-methylaniline → N4-(3,4-Dimethoxy-phenyl)-2,N4-dimethyl-quinazoline-4,6-diamine

HRID 1876203Notes

Reaction equation

HRID 1876203 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]([CH3:26])[C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([N+:22]([O-])=O)[CH:20]=3)[N:15]=[C:14]([CH3:25])[N:13]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].ClC1C2C(=CC=C([N+]([O-])=O)C=2)N=C(C)N=1.COC1C=C(NC)C=CC=1OC>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]([CH3:26])[C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH2:22])[CH:20]=3)[N:15]=[C:14]([CH3:25])[N:13]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 3

HCID 27869553,4-dimethoxy-N-methylanilineHCID 11653274(3,4-Dimethoxy-phenyl)-(2-methyl-6-nitro-quinazolin-4-yl)-methylamineHCID 249038664-Chloro-2-methyl-6-nitroquinazoline

Product 1

HCID 59242050N4-(3,4-Dimethoxy-phenyl)-2,N4-dimethyl-quinazoline-4,6-diamine

Procedure

(3,4-Dimethoxy-phenyl)-methyl-(2-methyl-6-nitro-quinazolin-4-yl)-amine: The title compound was prepared from 4-chloro-2-methyl-6-nitro-quinazoline (110 mg, 0.492 mmol) and (3,4-dimethoxy-phenyl)-methyl-amine (97 mg, 0.58 mmol) by a procedure similar to Example 177, with a final purification by MPLC (SiO2/0-100% EtOAc in CHCl3). LC-MS (ESI+; 355 ([M+H]+)).

Workup

  1. customwith a final purification by MPLC (SiO2/0-100% EtOAc in CHCl3)

Sources & evidence

ORD record
ord-d7f78a491a704e5498ac1db43a8d36a9
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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