2-Chloro-6,7-dimethoxy-4-quinazolinamine → HCID 53763865, compound

HRID 1288838Notes

Reaction equation

HRID 1288838 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4](Cl)[N:3]=1.[CH3:17][C:18]([CH3:36])([O:20][C:21]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][C@@H:24]1[C:29]([NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:22])[CH3:19]>CC(O)C>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:26]2[CH2:27][CH2:28][N:23]([C:21]([O:20][C:18]([CH3:17])([CH3:19])[CH3:36])=[O:22])[C@@H:24]([C:29]([NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25]2)[N:3]=1

Participants

4

Reactant 2

HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 54179194HCID 54179194, compound

Product 1

HCID 53763865HCID 53763865, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-amino-2-chloro-6,7-dimethoxyquinazoline (94.4 mg, 0.3939 mmol) and (R)-4-[(1,1-dimethylethoxy)carbonyl]-3-(1,1-dimethylethylamino) carbonyl piperazine (see Askin, D. et al., Tetrahedron Letters 1994, 35, 673-676) (112.4 mg, 0.3939 mol) in 2-propanol (1 mL) was heated at 90° C. (24 h). The solvent was removed in vacuo and the residue subjected to PCTLC (SiO2, 2 mm, 0-10% MeOH/CH2Cl2) which afforded ((R)-1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-[(1,1-dimethylethoxy)carbonyl]-3-(1,1-dimethylethylamino)carbonyl piperazine.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-63aa839ea93241a48757b006360bd5ac
Source dataset
uspto-grants-1998_05
Patent number
US05747490

Reaction notes

Loading…