Ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)-methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexylidene)acetate → Ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)-methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate

HRID 1913230Notes

Reaction equation

HRID 1913230 reaction equation
[CH3:1][Si:2]([CH3:38])([CH3:37])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:8]1[N:13]2[N:14]=[CH:15][CH:16]=[C:12]2[N:11]=[C:10]([CH:17]2[CH2:22][CH2:21][C:20](=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:19][CH2:18]2)[CH:9]=1>C(OCC)(=O)C>[CH3:36][Si:33]([CH3:34])([CH3:35])[CH2:32][CH2:31][O:30][CH2:29][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:38])([CH3:37])[CH3:1])[C:8]1[N:13]2[N:14]=[CH:15][CH:16]=[C:12]2[N:11]=[C:10]([CH:17]2[CH2:22][CH2:21][CH:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:19][CH2:18]2)[CH:9]=1

Participants

3

Reactant 1

HCID 66733552Ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)-methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexylidene)acetate

Product 1

HCID 66733619Ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)-methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetateYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 50 mL round-bottom flask was charged ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexylidene)acetate (Int-5j, 800 mg, 1.43 mmol) and ethyl acetate (15 mL). The flask was flushed with argon and 5% palladium on carbon (100 mg) was added. The flask was sealed and degassed under vacuum. Hydrogen gas was then added via balloon. The reaction was stirred under a hydrogen atmosphere 18 hours. The reaction was then filtered through celite to yield ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1.5-a]pyrimidin-5-yl)cyclohexyl)acetate (Int-5k) (761 mg, 1.35 mmol, 95% yield) as a pale yellow oil.

Workup

  1. customThe flask was flushed with argon and 5% palladium on carbon (100 mg)
  2. additionwas added
  3. customThe flask was sealed
  4. customdegassed under vacuum
  5. additionHydrogen gas was then added via balloon
  6. filtrationThe reaction was then filtered through celite

Sources & evidence

ORD record
ord-0028ace01b034aad91f54e1f38c4a56d
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

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