Piperidine → 5-[[7-(cyclopropylamino)-5-(3-hydroxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]methylidene]imidazolidine-2,4-dione

HRID 624713Notes

Reaction equation

[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:14]=O)=[C:9]3[N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=3)[CH:6]=2)[CH2:3][CH2:2]1.N1CCCCC1.[NH:29]1[CH2:35][C:33](=[O:34])[NH:32][C:30]1=[O:31]>CCO>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:14]=[C:35]4[NH:29][C:30](=[O:31])[NH:32][C:33]4=[O:34])=[C:9]3[N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=3)[CH:6]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

To 7-(cyclopropylamino)-5-(3hydroxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (100 mg, 0.340 mmol) in EtOH (2 mL) was added piperidine (67 μL, 0.680 mmol), and hydantoin (34 mg, 0.34 mmol). The reaction was stirred at 50° C. overnight. The solid formed was isolated by filtration to provide 70 mg of 5-((7-(cyclopropylamino)-5-(3-hydroxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione. (55%). LCMS (M+1=377)

Workup

customThe solid formed
customwas isolated by filtration

Sources & evidence

ORD record: ord-13bf044ab71a4ae1b969a1c364b91dc8
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

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