Thymidine → HCID 131728725, compound

HRID 871790Notes

Reaction equation

HRID 871790 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.[CH3:18][C:19]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C=O)C.O>[Si:22]([C@@:3]1([OH:4])[C@@H:5]([CH2:6][O:7][Si:22]([C:19]([CH3:21])([CH3:20])[CH3:18])([CH3:24])[CH3:23])[O:8][C@@H:1]([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:2]1)([C:19]([CH3:21])([CH3:20])[CH3:18])([CH3:24])[CH3:23]

Participants

5

Reactant 2

HCID 5789ThymidineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 131728725HCID 131728725, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of thymidine (5.00 g, 20.64 mmol) and imidiazole (9.0 g, 132.1 mmol) in anhydrous DMF (11 mL), a solution of TBSCl (9.96 g, 66.05 mmol) in DMF (11 mL) was added dropwise, and the mixture was stirred at room temperature overnight under a N2 atmosphere. After the mixture was diluted with water (100 mL), the formed precipitate was filtered and dissolved in ethyl ether (125 mL). The ether solution was washed twice with water (25 mL each) and once with brine (25 mL), dried over Na2SO4, and concentrated under reduced pressure to a waxy solid, which was re-crystallized from hexane/ethyl either (10:1) to yield 3′,5′-O-bis-tert-butyldimethylsilyl-thymidine dT.04 (10.64 g, 90%).

Workup

  1. filtrationthe formed precipitate was filtered
  2. dissolutiondissolved in ethyl ether (125 mL)
  3. washThe ether solution was washed twice with water (25 mL each) and once with brine (25 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure to a waxy solid, which
  6. customwas re-crystallized from hexane/ethyl either (10:1)

Sources & evidence

ORD record
ord-85725ec54ed3422cb34e2157f9020a30
Source dataset
uspto-grants-2015_03
Patent number
US08969535B2

Reaction notes

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