Water → HCID 86595762, compound

HRID 584789

Reaction equation

HRID 584789 reaction equation
[CH2:1]([CH:3]([N:6]1[C:14]2[N:13]3[N:15]=[C:16]([CH3:19])[C:17](I)=[C:12]3[N:11]=[C:10]([CH3:20])[C:9]=2[CH2:8][CH2:7]1)[CH2:4][CH3:5])[CH3:2].C[Si]([C:25]#[CH:26])(C)C.[F-].C[N+](C)(C)C.O>C(N(CC)CC)C.O1CCCC1.C(OCC)(=O)C.[Cu]I>[CH2:1]([CH:3]([N:6]1[C:14]2[N:13]3[N:15]=[C:16]([CH3:19])[C:17]([C:25]#[CH:26])=[C:12]3[N:11]=[C:10]([CH3:20])[C:9]=2[CH2:8][CH2:7]1)[CH2:4][CH3:5])[CH3:2]

Participants

9

Reactant 4

HCID 962WaterHCID 66111TrimethylsilylacetyleneHCID 67803Tetramethylammonium fluorideHCID 22249760HCID 22249760, compound

Product 1

HCID 86595762HCID 86595762, compoundYield 48.7%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 8-(1-ethylpropyl)-3-iodo-2,5-dimethyl-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine (2.0 g, 5.29 mmol), trimethylsilylacetylene (0.8 mL, 5.82 mmol), Cl2Pd(PPh3)2 (0.19 g, 0.26 mmol) and copper(I) iodide (50 mg, 0.26 mmol) in triethylamine (20 mL) was stirred at room temperature for two hours. The solution was filtered through Celite, and the filtrate was evaporated. Tetramethylammonium fluoride (1.0 M tetrahydrofuran solution 6.3 mL, 6.3 mmol) was added to a solution of the residue in tetrahydrofuran (20 mL) at room temperature, followed by stirring for 10 minutes. Water was added thereto, and the mixture was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (10-20% ethyl acetate/hexane), to give the title compound (727 mg) as pale brown crystals.

Workup

  1. filtrationThe solution was filtered through Celite
  2. customthe filtrate was evaporated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (10-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-19220f35d51b456db0176c70c05bcd77
Source dataset
uspto-grants-2005_08
Patent number
US06927221B2

Linked notes

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