Uridine → HCID 86587307, compound

HRID 2416150Notes

Reaction equation

HRID 2416150 reaction equation
[Si:1]([C@@:8]1([OH:32])[C@@H:12]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[O:11][C@@H:10]([N:22]2[CH:29]=[CH:28][C:26](=O)[NH:25][C:23]2=[O:24])[C@@H:9]1[O:30][CH3:31])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C@@H:33]1([N:42]2[CH:49]=[CH:48][C:46](=O)N[C:43]2=O)O[C@H](CO)[C@@H](O)[C@H:34]1O.CN1CCCCC1.C1(C)C=CC(S([Cl:66])(=O)=[O:64])=CC=1>C(#N)C.C(N(CC)CC)C>[Cl-:66].[Si:1]([C@@:8]1([OH:32])[C@@H:12]([CH2:13][O:14][Si:15]([C:18]([CH3:20])([CH3:19])[CH3:21])([CH3:16])[CH3:17])[O:11][C:10]([N:22]2[CH:29]=[CH:28][C:26]([N+:42]3([CH3:43])[CH2:33][CH2:34][CH2:46][CH2:48][CH2:49]3)=[N:25][C:23]2=[O:24])([OH:64])[C@@H:9]1[O:30][CH3:31])([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6029UridineHCID 73974-Toluenesulfonyl chlorideHCID 12291N-MethylpiperidineHCID 69539384HCID 69539384, compound

Product 1

HCID 86587307HCID 86587307, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent

Procedure

To the solution of 750 mg of 3′,5′-O-bis (t-butyldimethylsilyl)-2′-O-methyl uridine in 10 mL of acetonitrile was added 0.23 mL (1.2 times moles based on the uridine derivative) of 1-methylpiperidine and 0.45 mL of triethylamine, and the mixture was cooled. The solution of 614 mg of p-toluenesulfonyl chloride in 5 ml of acetonitrile was added dropwise with ice cooling, and the mixture was stirred for 1 hour. After the disappearance of the starting material, an 1 mL aliquot of the reaction solution was concentrated, and the residue was triturated with ether to remove the precipitated crystals by filtration. The filtrate was concentrated, and the residue was then washed with n-hexane and dried to give [[3,5-O-bis(t-butyldimethylsilyl)-2-O-methylribofuranos-1-yl]-2-oxo-1,2-dihydro-4-pyrimidinyl]-1-methylpiperidinium chloride (a reaction intermediate):

Workup

  1. temperaturethe mixture was cooled
  2. concentrationAfter the disappearance of the starting material, an 1 mL aliquot of the reaction solution was concentrated
  3. customthe residue was triturated with ether
  4. customto remove the precipitated crystals
  5. filtrationby filtration
  6. concentrationThe filtrate was concentrated
  7. washthe residue was then washed with n-hexane
  8. customdried

Sources & evidence

ORD record
ord-658e0a194213452087723b3fff48b89d
Source dataset
uspto-grants-2004_11
Patent number
US06822090B2

Reaction notes

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