N-(1-benzylpiperidine-4-yl)-2-(4,6-dimethyl-5-nitropyrimidine-2-ylamino)-N-methylacetamide → 2-(5-amino-4,6-dimethylpyrimidine-2-ylamino)-N-(1-benzylpiperidine-4-yl)-N-methylacetamide

HRID 2359500Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:30])[C:15](=[O:29])[CH2:16][NH:17][C:18]2[N:23]=[C:22]([CH3:24])[C:21]([N+:25]([O-])=O)=[C:20]([CH3:28])[N:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[NH2:25][C:21]1[C:22]([CH3:24])=[N:23][C:18]([NH:17][CH2:16][C:15]([N:14]([CH:11]2[CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][CH2:10]2)[CH3:30])=[O:29])=[N:19][C:20]=1[CH3:28]

Participants

Conditions

Temperature: 25 °C

Procedure

Compound 62 (93 mg) and zinc (147 mg) were suspended in acetic acid (2 mL) and the suspension was stirred at room temperature (20 to 30° C.) for 3 hours. Subsequently, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate: hexane=5:1 to 3:1) to give 25.4 mg (29% yield) of the desired product as a pale yellow amorphous.

Workup

filtrationSubsequently, the reaction mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (ethyl acetate: hexane=5:1 to 3:1)

Sources & evidence

ORD record: ord-73c4d494ab38422295b8a730e81b268d
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685989B2

Reaction notes

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