Trimethylsilylacetylene → HCID 67163888, compound

HRID 552772Notes

Reaction equation

HRID 552772 reaction equation
[C:1]([O:4][C@H:5]1[CH2:9][C@H:8]([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:13]=3[C:12](I)=[CH:11]2)[O:7][C@@H:6]1[CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])(=[O:3])[CH3:2].CCN(C(C)C)C(C)C.[C:46]([Si:48]([CH3:51])([CH3:50])[CH3:49])#[CH:47]>CN(C=O)C.CCOC(C)=O.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:4][C@H:5]1[CH2:9][C@H:8]([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:13]=3[C:12]([C:47]#[C:46][Si:48]([CH3:51])([CH3:50])[CH3:49])=[CH:11]2)[O:7][C@@H:6]1[CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])(=[O:3])[CH3:2]

Participants

8

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 67163817HCID 67163817, compound

Product 1

HCID 67163888HCID 67163888, compoundYield 58%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (2R,3S,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(5-iodo-4-phenethyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-tetrahydrofuran-3-yl acetate 9 obtained from example 132, step d) (0.36 g, 0.578 mmol), CuI (0.022 g, 0.0116 mmol), Pd(PPh3)2Cl2 (0.040 g, 0.0570 mmol) and DIPEA (0.20 mL, 1.15 mmol) in DMF was added ethynyltrimethylsilane (0.230 g, 2.34 mmol). The mixture was stirred at r.t. for 12 h. The reaction mixture was diluted with EtOAc. The organic layer was washed with H2O, dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography (0 to 25% EtOAc/hexanes) to give the title compound (0.305 g, 58%).

Workup

  1. washThe organic layer was washed with H2O
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (0 to 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7f47886925b3446bb750f41105861a2f
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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