Phenylacetylene → HCID 67166225, compound

HRID 552759Notes

Reaction equation

HRID 552759 reaction equation
I[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([CH2:21][NH:22][S:23]([NH2:26])(=[O:25])=[O:24])[O:12]1.[C:27]1([C:33]#[CH:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCN(C(C)C)C(C)C>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>[CH3:19][C:17]1([CH3:20])[O:16][C@H:15]2[C@H:11]([N:6]3[CH:5]=[N:4][C:3]4[C:7]3=[N:8][CH:9]=[N:10][C:2]=4[CH2:34][CH2:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:12][C@H:13]([CH2:21][NH:22][S:23]([NH2:26])(=[O:25])=[O:24])[C@H:14]2[O:18]1

Participants

7

Reactant 3

HCID 10821PhenylacetyleneHCID 81531DiisopropylethylamineHCID 86607332HCID 86607332, compound

Product 1

HCID 67166225HCID 67166225, compoundYield 60.2%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of N-{[(3aR,4R,6R,6aR)-6-(6-iodo-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl}sulfamide (0.14 g, 0.28 mmol) in DMF was added phenylacetylene (0.115 g, 1.13 mmol), CuI (10.6 mg, 0.056 mmol), DIPEA (98 μL, 0.56 mmol) and Pd(PPh3)2Cl2 (10 mg, 0.028 mmol) The solution was stirred for 1 h at r.t. and concentrated. The residue was taken up in DCM, washed with saturated aq EDTA.Na2 (3×20 mL), dried (Na2SO4) concentrated and purified by flash chromatography (20 to 60% EtOAc/DCM) to give the title compound (0.08 g, 60%).

Workup

  1. concentrationconcentrated
  2. washwashed with saturated aq EDTA
  3. dry with materialNa2 (3×20 mL), dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by flash chromatography (20 to 60% EtOAc/DCM)

Sources & evidence

ORD record
ord-df42b5c7a6e54a1aaeadc18dee1cfa49
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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