Hydrochloric Acid → HCID 86711296, compound

HRID 336165Notes

Reaction equation

HRID 336165 reaction equation
[ClH:1].[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2[C:20]3[C:19]([NH2:21])=[N:18][CH:17]=[N:16][C:15]=3[N:14](COCC[Si](C)(C)C)[CH:13]=2)[CH:3]=1.C(OCC)(=O)C>C(O)C>[ClH:1].[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2[C:20]3[C:19]([NH2:21])=[N:18][CH:17]=[N:16][C:15]=3[NH:14][CH:13]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid3×HCID 8857Ethyl AcetateHCID 86711298HCID 86711298, compound

Product 1

HCID 86711296HCID 86711296, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Concentrated hydrochloric acid (20 ml) was added at 90° C. to a solution of 5-(quinolin-3-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (10.0 g) obtained in Step 3 in ethanol (200 ml), and the mixture was stirred at the same temperature for 25 minutes. Subsequently, concentrated hydrochloric acid (30 ml) was added thereto, and the mixture was stirred at the same temperature for 75 minutes. After the reaction mixture was cooled, ethanol (100 ml) was added thereto, and stirred at 95° C. for 90 minutes. Subsequently, ethanol (100 ml) and concentrated hydrochloric acid (25 ml) were added, and the mixture was stirred at the same temperature for 4 days. After the reaction mixture was cooled, ethyl acetate was added thereto. The resulting precipitate was then collected by filtration, washed with ethyl acetate, and dried under reduced pressure to obtain the title compound (4.4 g) as a yellow solid.

Workup

  1. stirringthe mixture was stirred at the same temperature for 75 minutes
  2. temperatureAfter the reaction mixture was cooled
  3. stirringstirred at 95° C. for 90 minutes
  4. stirringthe mixture was stirred at the same temperature for 4 days
  5. temperatureAfter the reaction mixture was cooled
  6. filtrationThe resulting precipitate was then collected by filtration
  7. washwashed with ethyl acetate
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-c4a0cbfffd9b4d0c94212e7f36f0de06
Source dataset
uspto-grants-2014_11
Patent number
US08889666B2

Reaction notes

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