N-Methyl-4-anisidine → (2-Chloro-6-nitroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine

HRID 1876183Notes

Reaction equation

HRID 1876183 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=2)[N:3]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][CH3:25])=[CH:20][CH:19]=1.CC([O-])=O.[Na+]>C1COCC1.O>[Cl:1][C:2]1[N:11]=[C:10]([N:24]([C:21]2[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[CH3:25])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 22250N-Methyl-4-anisidineHCID 517045Sodium AcetateHCID 127033662,4-Dichloro-6-nitroquinazoline

Product 1

HCID 11609884(2-Chloro-6-nitroquinazolin-4-yl)-(4-methoxyphenyl)-methylamineYield 79.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.65 g (6.76 mmol) of 2,4-dichloro-6-nitro-quinazoline, 1.02 g (7.44 mmol) of (4-methoxy-phenyl)-methyl-amine, 0.6 g (7.43 mmol) of NaOAc in 6 mL of THF and 6 mL of water was stirred at ambient temperature for 18 hours. The reaction mixture extracted with EtOAc (2×15 mL) and organics were washed with NaHCO3, dried and concentrated. Isolation done by MPLC (0-30% EtOAc/hexanes as eluent) to give 1.86 g of the title compound. 1H NMR (DMSO-d6) δ 8.38-7.13 (7H), 3.84 (s, 3H), 3.59 (s, 3H); LC-MS (ESI+; 345 ([M+H]+)).

Workup

  1. extractionThe reaction mixture extracted with EtOAc (2×15 mL)
  2. washorganics were washed with NaHCO3
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-608cac3bfd7745e4a3b6f376acfb19ba
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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