Triethylamine → HCID 54000360, compound

HRID 1168689Notes

Reaction equation

HRID 1168689 reaction equation
I[C:2]1[C:3]([NH2:17])=[N: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(N([CH2:23][CH3:24])CC)C.[C:25](O)(=[S:27])C>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>[SH:27][CH2:25][C:23]#[C:24][C:2]1[C:3]([NH2:17])=[N: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

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 65050IbacitabineHCID 178418634HCID 178418634, compound

Product 1

HCID 54000360HCID 54000360, compoundYield 88%

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-2′-deoxycytidine (Sigma, 92 mg, 0.260 mmol) and Pd(PPh3)4 (30 mg, 0.026 mmol) in absolute DMF (1.3 mL) was treated sequentially with triethylamine (0.072 mL, 53 mg, 0.520 mmol), the propargyl S-thioester of thioacetic acid (74 mg, 0.650 mmol), and CuI (10 mg, 0.052 mmol). The mixture was stirred at RT (4 h), the solvents were removed in high vacuum, and the residue was chromatographed (silica, CH2Cl2:MeOH 9:1) to yield the S-acetate of 5-(3-mercaptopropyn-1-yl)-2′-deoxycytidine (77 mg, 0.227 mmol, 88%) as a light yellow oil.

Workup

  1. customthe solvents were removed in high vacuum
  2. customthe residue was chromatographed (silica, CH2Cl2:MeOH 9:1)

Sources & evidence

ORD record
ord-088b94b46991472ca06a8667815104c1
Source dataset
uspto-grants-2003_09
Patent number
US06627456B1

Reaction notes

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