Triethylamine → HCID 68561395, compound

HRID 19468Notes

Reaction equation

HRID 19468 reaction equation
[C@@H:1]1([C:10]2[C:11](=[O:17])[NH:12][CH:13]=[C:14](I)[CH:15]=2)[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3].C(N(CC)CC)C.[C:25]1([C:31]#[CH:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(OCC)(=O)C>CN(C=O)C.[Cu]I.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>[C@@H:1]1([C:10]2[C:11](=[O:17])[NH:12][CH:13]=[C:14]([C:32]#[C:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:15]=2)[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10821PhenylacetyleneHCID 67241648HCID 67241648, compound

Product 1

HCID 68561395HCID 68561395, compoundYield 92%

Reagents, catalysts & solvents 3

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

Procedure

3-(β-D-Ribofuranosyl)-5-iodopyridin-2(1H)-one prepared in Example 1(1) (71 mg, 0.20 mmol) was dissolved in DMF (1.0 ml), followed by addition of CuI (6 mg, 0.032 mmol), triethylamine (42 μl, 0.30 mmol), phenylacetylene (33 μl, 0.30 mmol) and Pd(Ph3P)4 (11 mg, 0.010 mol). The reaction mixture was stirred under an argon atmosphere at room temperature for 6 hours. After addition of ethyl acetate (10 ml), the reaction mixture was extracted three times with water (10 ml each). The combined aqueous layers were concentrated under reduced pressure and then purified by reversed-phase HPLC to give 3-(β-D-ribofuranosyl)-5-(2-phenylethynyl)-pyridin-2(1H)-one (60 mg, 92%) as a white product.

Workup

  1. extractionthe reaction mixture was extracted three times with water (10 ml each)
  2. concentrationThe combined aqueous layers were concentrated under reduced pressure
  3. custompurified by reversed-phase HPLC

Sources & evidence

ORD record
ord-2c19a1711fba4c5397acf16d58cb87be
Source dataset
uspto-grants-2010_06
Patent number
US07745417B2

Reaction notes

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