Thymidine → HCID 68806946, compound

HRID 2180218Notes

Reaction equation

HRID 2180218 reaction equation
[C@@H:1]1([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.C(N(CC)CC)C.C(#N)C=C>N1C=CC=CC=1>[C:1](#[N:9])[CH:2]=[CH2:3].[C@@H:1]1([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1

Participants

5

Reactant 3

HCID 5789ThymidineHCID 7855AcrylonitrileHCID 8471Triethylamine

Product 1

HCID 68806946HCID 68806946, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of thymidine (0.48 g, 2 mmol), triethylamine (20 ml) and dry pyridine (20 ml) was added freshly distilled acrylonitrile (1 ml, 15 mmol). After heating at 50° C. for 24 hours, the reaction mixture was cooled, concentrated, and purified by flash chromatography using dichloromethane:ethylacetate:methanol (85:15:5) as the mobile phase. Appropriate fractions were collected and concentrated to give the desired adduct as a colorless solid in 47% yield having a m.pt. of 114-116° C. The product exhibited the expected spectroscopic profile in 1H NMR and 13C NMR.

Workup

  1. temperaturethe reaction mixture was cooled
  2. concentrationconcentrated
  3. custompurified by flash chromatography
  4. customAppropriate fractions were collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0dd6a2aefa584038a114239cd2f5a14b
Source dataset
uspto-grants-2005_05
Patent number
US06887990B1

Reaction notes

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