Triethylamine → HCID 71589304, compound

HRID 473243Notes

Reaction equation

HRID 473243 reaction equation
I[C:2]1[C:3](=[O:22])[NH:4][C:5](=[O:21])[N:6]([CH:20]=1)[C@@H:7]1[O:19][C@H:10]([CH2:11][O:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:9][CH2:8]1.[CH:23]1[C:40]2=[C:41]3[C:30]([C:31]4[C:42]5[C:35](=[CH:36][CH:37]=[CH:38][C:39]2=5)[CH:34]=[CH:33][CH:32]=4)=[CH:29][CH:28]=[CH:27][C:26]3=[C:25]([C:43]#[CH:44])[CH:24]=1.CCN(CC)CC>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH:23]1[C:40]2=[C:41]3[C:30]([C:31]4[C:42]5[C:35](=[CH:36][CH:37]=[CH:38][C:39]2=5)[CH:34]=[CH:33][CH:32]=4)=[CH:29][CH:28]=[CH:27][C:26]3=[C:25]([C:43]#[C:44][C:2]2[C:3](=[O:22])[NH:4][C:5](=[O:21])[N:6]([CH:20]=2)[C@@H:7]2[O:19][C@H:10]([CH2:11][O:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:9][CH2:8]2)[CH:24]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 1255323-EthynylperyleneHCID 69044757HCID 69044757, compound

Product 1

HCID 71589304HCID 71589304, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-iodo-5′-O-pivaloyl-2′,3′-dideoxyuridine (442 mg, 1 mmol) and 3-perylenylacetylene (345 mg, 1.25 mmol) in 10 mL of DMF was degassed three times by alternation between vacuum and argon. Then Pd(PPh3)4 (115 mg, 0.1 mmol), CuI (38 mg, 0.2 mmol) and Et3N (0.278 mL, 2 mmol) were added and the flask was degassed once again, filled with argon, and the mixture was stirred for 43 hours at ambient temperature. The mixture was diluted with 300 mL of EtOAc, washed 3×200 mL of water, dried with Na2SO4, and evaporated. Chromatography on a silica gel column using a 0 to 2% of EtOH/CHCl3 gradient gave rise to a chromatographically homogeneous (Rf 0.28, 5% EtOH/CHCl3) product as orange foam (545 mg, 96%). 1H-NMR (DMSO-d6): 11.85 (s, 1H, NH), 8.44 (d, 1H, J 7.8), 8.39-8.35 (m, 3H), 8.32 (d, 1H, J 8.2) (perylenyl), 8.06 (s, 1H, H-6), 7.83-7.81 (m, 2H), 7.69-7.60 (m, 2H), 7.58-7.53 (m, 2H) (perylenyl), 6.00 (dd, 1H, J1′,2′α 6.9 J1′,2′β 4.6, H-1′), 4.37-4.34 (m, 1H, H-4′), 4.32-4.26 (m, 2H, H-5′), 2.42-2.36 (m, 1H, H-2′), 2.17-2.12 (m, 1H, H-2′), 2.06-2.00 (m, 1H, H-3′), 1.90-1.83 (m, 1H, H-3′), 1.17 (s, 9H, tBu).

Workup

  1. customthe flask was degassed once again
  2. additionfilled with argon
  3. additionThe mixture was diluted with 300 mL of EtOAc
  4. washwashed 3×200 mL of water
  5. dry with materialdried with Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-e1a695ce314140398ea2c53729de9921
Source dataset
uspto-grants-2014_01
Patent number
US08633308B2

Reaction notes

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