Ethanol → HCID 178507871, compound

HRID 624688Notes

Reaction equation

HRID 624688 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-03b038ec145f4a36af678eda76d40f31
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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