Water → HCID 86595762, compound

HRID 890174Notes

Reaction equation

HRID 890174 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 222497608-(1-Ethylpropyl)-3-iodo-2,5-dimethyl-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine

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-f0255a733e484539a2400a694125656f
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

Loading…