Hydrochloric Acid → HCID 135593031, compound

HRID 584820Notes

Reaction equation

HRID 584820 reaction equation
Cl.C([N:9]1[C:17]2[N:16]3[N:18]=[C:19]([CH3:30])[C:20]([C:21]4[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=4[CH3:29])=[C:15]3[N:14]=[C:13]([CH3:31])[C:12]=2[CH2:11][CH2:10]1)C1C=CC=CC=1.O.C(O)C>[H][H].[C].[Pd]>[C:26]1([CH3:27])[CH:25]=[C:24]([CH3:28])[CH:23]=[C:22]([CH3:29])[C:21]=1[C:20]1[C:19]([CH3:30])=[N:18][N:16]2[C:17]3[NH:9][CH2:10][CH2:11][C:12]=3[C:13]([CH3:31])=[N:14][C:15]=12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 22249937HCID 22249937, compound

Product 1

HCID 135593031HCID 135593031, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

Concentrated hydrochloric acid (1 mL) was added to a mixture of 8-benzyl-3-mesityl-2,5-dimethyl-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine (4.7 g) which is a free compound of the compound prepared in Example 26, water-containing 5% palladium carbon (3.0 g) and ethanol (300 mL), followed by stirring at room temperature for two days in hydrogen atmosphere. After filtering through Celite, the filtrate was evaporated, which was neutralized with an aqueous solution of sodium bicarbonate. The resulting solid was filtered, and dissolved in a mixed solution of dichloromethane, methanol and ethyl acetate. After filtering off the insoluble matter, the mixture was purified by silica gel column chromatography (10-67% ethyl acetate/hexane), to give the title compound as white crystals (2.6 g). 1.0 g of a raw material was recovered.

Workup

  1. filtrationAfter filtering through Celite
  2. customthe filtrate was evaporated
  3. filtrationThe resulting solid was filtered
  4. dissolutiondissolved in a mixed solution of dichloromethane, methanol and ethyl acetate
  5. filtrationAfter filtering off the insoluble matter
  6. customthe mixture was purified by silica gel column chromatography (10-67% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ac5292e9a70d40a991ac661393af93bd
Source dataset
uspto-grants-2005_08
Patent number
US06927221B2

Reaction notes

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