N-methyl-2-pyrrolidone → 2-{[(1-Aminocyclohexyl)methyl]amino}-4-{[3-(methylcarbamoyl)phenyl]amino}-6-oxo-1,6-dihydropyrimidine-5-carboxamide

HRID 869267Notes

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:13]=[C:14](S(C)=O)[NH:15][C:16](=[O:21])[C:17]=2[C:18]([NH2:20])=[O:19])[CH:8]=[CH:9][CH:10]=1)=[O:4].[NH2:25][CH2:26][C:27]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.CN1C(=O)CCC1>C(OCC)(=O)C>[NH2:33][C:27]1([CH2:26][NH:25][C:14]2[NH:15][C:16](=[O:21])[C:17]([C:18]([NH2:20])=[O:19])=[C:12]([NH:11][C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([C:3](=[O:4])[NH:2][CH3:1])[CH:6]=3)[N:13]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-{[3-(methylcarbamoyl)phenyl]amino}-2-(methylsulfinyl)-6-oxo-1,6-dihydropyrimidine-5-carboxamide (Preparation Example 311) (234 mg), 1-(aminomethyl)cyclohexaneamine (172 mg) and NMP (2 mL) was stirred at 80° C. for 30 minutes. After cooling, the reaction liquid was diluted with ethyl acetate, and the precipitated solid was collected by filtration. This solid was heated with ethanol-water and washed to give 2-{[(1-aminocyclohexyl)methyl]amino}-4-{[3-(methylcarbamoyl)phenyl]amino}-6-oxo-1,6-dihydropyrimidine-5-carboxamide (215 mg) as a white solid.

Workup

temperatureAfter cooling
customthe reaction liquid
filtrationthe precipitated solid was collected by filtration
temperatureThis solid was heated with ethanol-water
washwashed

Sources & evidence

ORD record: ord-bbfc9d00c43c45e39b88ead7400fd8b8
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969336B2

Reaction notes

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