Toluene → HCID 136133166, compound

HRID 1914817Notes

Reaction equation

HRID 1914817 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[CH:4][C:3]=1[CH:12]=O.[C:14]1([CH2:20][C:21](OC)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC(C)([O-])C.[K+].C1(C)C=CC=CC=1>CN(C=O)C>[CH3:11][C:9]1[CH:10]=[C:6]2[N:5]=[CH:4][C:3]3[CH:12]=[C:20]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:21](=[O:22])[NH:1][C:2]=3[N:7]2[N:8]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 7559Methyl phenylacetateHCID 23665647Potassium tert-butoxideHCID 58034374HCID 58034374, compound

Product 1

HCID 136133166HCID 136133166, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

Into a round bottom flask was added 7-amino-2-methylpyrazolo[1,5-a]pyrimidine-6-carbaldehyde (1-2) (5.30 g, 30 mmol), methy phenylacetate (18.0 g, 120 mmol), potassium tert-butoxide (5.80 g, 60 mmol), and toluene (100 mL). The reaction mixture was heated to 105° C. while stirring under an atmosphere of nitrogen for 30 min. Then DMF (100 mL) was added and the mixture was stirred at 100° C. for 3 days. The reaction mixture was cooled to room temperature and concentrated in vacuo. The resulting residue was dissolved in DCM (600 mL) and then water (400 mL) was added to the solution. The precipitated solid was collected by filtration and the solid was washed with water (50 mL) and DCM (100 mL). The solid was dried over an oil pump for 2 days to give 2-methyl-7-phenylpyrazolo[1,5-a]pyrido[3,2-e]pyrimidin-8(9H)-one (1-3) as a yellow solid.

Workup

  1. stirringthe mixture was stirred at 100° C. for 3 days
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resulting residue was dissolved in DCM (600 mL)
  5. additionwater (400 mL) was added to the solution
  6. filtrationThe precipitated solid was collected by filtration
  7. washthe solid was washed with water (50 mL) and DCM (100 mL)
  8. customThe solid was dried over an oil pump for 2 days

Sources & evidence

ORD record
ord-c2e5c5587a834238a2740dc8115aa09a
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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