Thymidine → 1-[2-Deoxy-5-O-(triphenylmethyl)pentofuranosyl]-5-methylpyrimidine-2,4(1H,3H)-dione

HRID 2181377Notes

Reaction equation

HRID 2181377 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C@@H:21]1([N:29]2[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]2=[O:31])[O:28][C@H:25]([CH2:26][OH:27])[C@@H:23]([OH:24])[CH2:22]1>N1C=CC=CC=1>[C:1]([O:27][CH2:26][C@H:25]1[O:28][C@@H:21]([N:29]2[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]2=[O:31])[CH2:22][C@@H:23]1[OH:24])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5789ThymidineHCID 6456Trityl chloride

Product 1

HCID 5141781-[2-Deoxy-5-O-(triphenylmethyl)pentofuranosyl]-5-methylpyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

In a 250-ml three-necked flask, trityl chloride is placed in anhydrous pyridine under inert gas and stirring, and the thymidine is added. After 30 minutes of heating to t=110° C. (heating-bath temperature), the yellowish reaction solution is allowed to cool and is then decanted slowly into 1.5 l of vigorously stirred ice water. After 30 minutes of stirring, the milky-white suspension is suction-filtered, the filter cake is dissolved in acetone and the solution is filtered once again. The solvent is removed in the rotary evaporator and the solid is dried for 16 hours in high vacuum. The product, 5′-O-tritylthymidine, is obtained by recrystallization two times from a benzene-acetone mixture.

Workup

  1. temperatureto cool
  2. customis then decanted slowly into 1.5 l of vigorously stirred ice water
  3. stirringAfter 30 minutes of stirring
  4. filtrationthe milky-white suspension is suction-filtered
  5. dissolutionthe filter cake is dissolved in acetone
  6. filtrationthe solution is filtered once again
  7. customThe solvent is removed in the rotary evaporator
  8. customthe solid is dried for 16 hours in high vacuum

Sources & evidence

ORD record
ord-1da5c18294764affb013c52b3a29b166
Source dataset
uspto-grants-2005_05
Patent number
US06891033B2

Reaction notes

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