Ethanol → HCID 178507871, compound

HRID 2036918Notes

Reaction equation

HRID 2036918 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([CH:11]=O)=[C:6]2[N:5]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[CH:3]=1.C(O)C.[NH:24]1[CH2:30][C:28](=[O:29])[NH:27][C:25]1=[O:26].N1CCCCC1>O>[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([CH:11]=[C:30]3[NH:24][C:25](=[O:26])[NH:27][C:28]3=[O:29])=[C:6]2[N:5]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8082PiperidineHCID 10006HydantoinHCID 58313936HCID 58313936, compound

Product 1

HCID 178507871HCID 178507871, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To the reaction vial, 7-amino-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (411 mg, 1.4 mmol) was added to ethanol (5.2 mL) along with hydantoin (143 mg, 1.4 mmol) and piperidine (141 μL, 1.4 mmol). The reaction was heated at 80° C. for 60 minutes in the microwave. The reaction was then cooled to room temperature and diluted with water. The solid was collected by filtration, washed with water and cold ethanol. The material was dried under vacuum overnight. The product, 5-((7-amino-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione, was recovered as a red solid in 54% yield. LCMS (M+1=370)

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. filtrationThe solid was collected by filtration
  3. washwashed with water and cold ethanol
  4. customThe material was dried under vacuum overnight
  5. customThe product, 5-((7-amino-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione, was recovered as a red solid in 54% yield

Sources & evidence

ORD record
ord-691a5349a68548e799dbd0872742e0c0
Source dataset
uspto-grants-2013_11
Patent number
US08575177B2

Reaction notes

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