Ammonium Hydroxide → 139888-11-2

HRID 1613143Notes

Reaction equation

HRID 1613143 reaction equation
[C:1]([C@:3]1([CH2:18][O:19]C(=O)C)[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:17])#[N:2].[NH4+].[OH-]>CO>[C:1]([C@:3]1([CH2:18][OH:19])[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:17])#[N:2]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 18650256HCID 18650256, compound

Product 1

HCID 452277139888-11-2Yield 40.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4'-cyano-5'-O-acetylthymidine (0.85 g, 2.76 mM) and NH4OH (15 ml) in CH3OH (15 ml) was stirred at 24° C. for 2 hours. The solvent was removed by evaporation under pump vacuum. The residue was purified by flash chromatography on silica gel eluting with (7% CH3OH/CH2Cl2) and by preparative chromatography TLC affording 4'-cyanothymidine (300 mg, 1.12 mM). mp 238.5° C. to 242.5° C.

Workup

  1. customThe solvent was removed by evaporation under pump vacuum
  2. customThe residue was purified by flash chromatography on silica gel eluting with (7% CH3OH/CH2Cl2) and by preparative chromatography TLC

Sources & evidence

ORD record
ord-82fc5a100fed4039b7430421385ad4e1
Source dataset
uspto-grants-1993_03
Patent number
US05192749

Reaction notes

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