4-Ethoxy-7,9-dimethyl-8-(4-nitrobenzyl)-2-piperazin-1-yl-pyrido[3',2':4,5]thieno[3,2-d]pyrimidine → 8-(4-Aminobenzyl)-4-ethoxy-7,9-dimethyl-2-piperazin-1-yl-pyrido[3',2':4,5]thieno[3,2-d]pyrimidine
Reaction equation
[OH-].[NH3+]N.[CH2:4]([O:6][C:7]1[C:8]2[S:21][C:20]3[N:22]=[C:23]([CH3:37])[C:24]([CH2:27][C:28]4[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][CH:29]=4)=[C:25]([CH3:26])[C:19]=3[C:9]=2[N:10]=[C:11]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[N:12]=1)[CH3:5]>C(O)C.[Pd]>[NH2:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][C:24]2[C:23]([CH3:37])=[N:22][C:20]3[S:21][C:8]4[C:7]([O:6][CH2:4][CH3:5])=[N:12][C:11]([N:13]5[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]5)=[N:10][C:9]=4[C:19]=3[C:25]=2[CH3:26])=[CH:29][CH:30]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
40 mg 10% Pd/C and 0.5 ml (10 mmol) hydraziniumhydroxide are added to 0.36 g (0.8 mmol) 4-ethoxy-7,9-dimethyl-8-(4-nitrobenzyl)-2-piperazin-1-yl-pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine in 3 ml ethanol. Then, refluxing is carried for 10 h, the solvent is removed and the residue is taken up with 50 ml chloroform. Following filtration, the solvent is removed and the residue is recrystallized from chloroform/cyclohexane. 0.16 g (45%) of the title substance is obtained.
Workup
- temperatureThen, refluxing
- customthe solvent is removed
- filtrationfiltration
- customthe solvent is removed
- customthe residue is recrystallized from chloroform/cyclohexane
- custom0.16 g (45%) of the title substance is obtained
Sources & evidence
- ORD record
- ord-a2020dcb98cf4e7abd4ee502d174d483
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08058285B2
Reaction notes
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