Phenylacetylene → HCID 67165314, compound

HRID 552744Notes

Reaction equation

HRID 552744 reaction equation
[C:1]([O:4][C@H:5]1[CH2:9][C@H:8]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3Br)[O:7][C@@H:6]1[CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])(=[O:3])[CH3:2].CCN(C(C)C)C(C)C.[C:38]1([C:44]#[CH:45])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CN(C=O)C.[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[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[C:45]#[C:44][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:7][C@@H:6]1[CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 10821PhenylacetyleneHCID 81531DiisopropylethylamineHCID 86607294HCID 86607294, compound

Product 1

HCID 67165314HCID 67165314, compoundYield 91.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of (2R,3S,5R)-5-(6-bromo-9H-purin-9-yl)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-3-yl acetate (1.26 g, 2.67 mmol), CuI (0.102 g, 0.534 mmol), and Pd(PPh3)2Cl2 (0.187 g, 0.267 mmol) in DMF was added DIPEA (0.930 mL, 5.34 mmol) and phenylacetylene (1.17 mL, 10.69 mmol). The mixture was stirred at 75° C. for 1 hour then concentrated. The residue was dissolved in CH2Cl2 (70 mL) and washed with saturated aq EDTA.Na2 (3×50 mL). The combined organics were dried (Na2SO4) and concentrated. The dark crude oil was purified by flash chromatography (40% EtOAc/hexanes) to afford the title compound (1.2 g, 91%).

Workup

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in CH2Cl2 (70 mL)
  3. washwashed with saturated aq EDTA
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe dark crude oil was purified by flash chromatography (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7de00b26b3be47d1b77cc68106d146db
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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