Bicarbonate Ion → HCID 11493075, compound

HRID 1781570Notes

Reaction equation

HRID 1781570 reaction equation
I[C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1.[CH:18]#[C:19][CH2:20][CH2:21][CH3:22].CO.C(=O)(O)[O-]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I.C(Cl)Cl>[C:18]([C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1)#[C:19][CH2:20][CH2:21][CH3:22]

Participants

8

Reactant 4

HCID 769Bicarbonate IonHCID 887MethanolHCID 5905IdoxuridineHCID 123091-Pentyne

Product 1

HCID 11493075HCID 11493075, compoundYield 81.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

This compound was prepared by the same procedure that Hobbs, F. W. J., J Org Chem (1989) 54: 3420-3422, used for the preparation of other alkynyl substituted nucleosides. A mixture of 30.0 g (84.7 mmol) of 5-iodo-2'deoxyuridine (purchased from Sigma), 23.6 mL of 1-pentyne (Aldrich), 9.79 g of tetrakis (triphenylphosphine) palladium (0) (Aldrich), and 3.23 g of copper (I) iodide were stirred at room temperature for 26 h. To the reaction was added 250 mL of MeOH and 250 mL of CH2Cl2. The mixture was neutralized with Dowex 1 x 8-200 (bicarbonate form) ion exchange resin. The mixture was filtered and concentrated. The residue was partitioned between H2O and CH2Cl2. The aqueous layer was extracted three times with CH2Cl2 and then concentrated. Purification of the crude product by column chromatography afforded 20.4 g (81.9% yield) of product.

Workup

  1. customThis compound was prepared by the same procedure that Hobbs, F
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customThe residue was partitioned between H2O and CH2Cl2
  5. extractionThe aqueous layer was extracted three times with CH2Cl2
  6. concentrationconcentrated
  7. customPurification of the crude product by column chromatography

Sources & evidence

ORD record
ord-f301d0b9494940d59d0901c5a8aebf22
Source dataset
uspto-grants-1997_05
Patent number
US05633360

Reaction notes

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