Triethylamine → HCID 54000360, compound

HRID 1738755Notes

Reaction equation

HRID 1738755 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-4e08f5544e8141a683f7093dbd73ff23
Source dataset
uspto-grants-1999_10
Patent number
US05965364

Reaction notes

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