Ethanol → HCID 178518518, compound

HRID 624732Notes

Reaction equation

[CH2:1]([S:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([CH:18]=O)=[C:13]2[N:12]=[C:11]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[NH:31]1[CH2:37][C:35](=[O:36])[NH:34][C:32]1=[O:33].N1CCCCC1>O>[CH2:1]([S:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([CH:18]=[C:37]3[NH:31][C:32](=[O:33])[NH:34][C:35]3=[O:36])=[C:13]2[N:12]=[C:11]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To the reaction flask, 7-(benzylthio)-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (3.7 g, 9.3 mmol) was added to ethanol (31 mL) along with hydantoin (933 mg, 9.3 mmol) and piperidine (920 μL, 9.3 mmol). The reaction was heated at 80° C. for 3 days then cooled to room temperature and diluted with water. The solid was collected by filtration, washed with water, 50% ethanol/water, and then 100% ethanol. The material was dried under vacuum overnight. The product, 5-((7-(benzylthio)-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione, was recovered as a yellow solid in 92% yield. LCMS (M+1=477)

Workup

temperaturethen cooled to room temperature
filtrationThe solid was collected by filtration
washwashed with water, 50% ethanol/water
customThe material was dried under vacuum overnight
customThe product, 5-((7-(benzylthio)-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione, was recovered as a yellow solid in 92% yield

Sources & evidence

ORD record: ord-fa70866a4b864f2292370481a3aa46f7
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

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