4-Chlorobenzylamine → HCID 67282640, compound

HRID 1616116Notes

Reaction equation

HRID 1616116 reaction equation
Cl[C:2]1[N:11]([CH3:12])[C:10](=[O:13])[C:9]2[C:4](=[CH:5][C:6]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.[Cl:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=1>C(O)(C)C>[Cl:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH:33][C:2]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]3[C:4](=[CH:5][C:6]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][CH:8]=3)[N:3]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 660364-ChlorobenzylamineHCID 81531DiisopropylethylamineHCID 67282409HCID 67282409, compound

Product 1

HCID 67282640HCID 67282640, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of methyl 2-chloro-3-methyl-4-oxo-3,4-dihydroquinazoline-7-carboxylate (70.0 mg, 0.28 mmol) in isopropyl alcohol (3 mL) was added N,N-diisopropylethylamine (0.10 mL, 0.58 mmol) and p-chlorobenzylamine (84.2 μL, 0.69 mmol). The reaction mixture was heated to 100° C. and stirred for 1 h. The mixture was then cooled to rt and concentrated. The residue was purified by flash silica gel chromatography (0% to 5% MeOH/DCM) to afford methyl 2-[(4-chlorobenzyl)amino]-3-methyl-4-oxo-3,4-dihydroquinazoline-7-carboxylate (92 mg, 93%). LC-MS: (FA) ES+ 358.

Workup

  1. temperatureThe mixture was then cooled to rt
  2. concentrationconcentrated
  3. customThe residue was purified by flash silica gel chromatography (0% to 5% MeOH/DCM)

Sources & evidence

ORD record
ord-96475c9dfb6b4707b0b8eccc8b07a386
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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