Trimethylsilylacetylene → HCID 20778052, compound

HRID 1816512Notes

Reaction equation

HRID 1816512 reaction equation
I[C:2]1[C:3](=[O:38])[NH:4][C:5](=[O:37])[N:6]([CH:36]=1)[C@@H:7]1[O:35][C@H:11]([CH2:12][O:13][C:14]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C@@H:9]([OH:10])[CH2:8]1.[Si:39]([C:43]#[CH:44])([CH3:42])([CH3:41])[CH3:40]>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.[Cu]I>[CH3:40][Si:39]([C:43]#[C:44][C:2]1[C:3](=[O:38])[NH:4][C:5](=[O:37])[N:6]([CH:36]=1)[C@@H:7]1[O:35][C@H:11]([CH2:12][O:13][C:14]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C@@H:9]([OH:10])[CH2:8]1)([CH3:42])[CH3:41]

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 18667132HCID 18667132, compound

Product 1

HCID 20778052HCID 20778052, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

2 g of 2′-deoxy-5-iodo-5′-O-(4-methoxytrityl)-uridine (3.19 mmole) prepared in 1-1) together with (PPh3)2PdCl2 (0.1 eq) and 61 mg of CuI (0.1 eq), were dried under a vacuum, TEA and THF in a ratio of 3:1 were added thereto, and the mixture was purged several times with argon. 0.59 ml of TMS-acetylene (1.3 eq) was then added to the mixture at a temperature ranging from 45 to 50° C., until it became black. The resulting mixture was heated for additional 3 hours to terminate the reaction, and subjected to column chromatography (silica gel 60, 230˜400 meshes, Merck) to obtain the title compound as a pale yellow solid. The chromatography was conducted using a mixture of hexane and ethyl acetate as an elution solution whose mix ratio was gradually varied from 3:1 to 1:1 (v/v).

Workup

  1. dry with materialwere dried under a vacuum, TEA and THF in a ratio of 3:1
  2. additionwere added
  3. customthe mixture was purged several times with argon
  4. customranging from 45 to 50° C., until it
  5. temperatureThe resulting mixture was heated for additional 3 hours
  6. customto terminate
  7. customthe reaction

Sources & evidence

ORD record
ord-a6c6183a8a604c8ab48a749bd4acaf4b
Source dataset
uspto-grants-2005_04
Patent number
US06884882B1

Reaction notes

Loading…