Pyridine → HCID 67259612, compound

HRID 2105885Notes

Reaction equation

HRID 2105885 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][C:9]1[CH:47]=[CH:46][C:12]([C:13]([O:28][CH2:29][C@H:30]2[O:34][C@@H:33]([C:35]3[C:41](=[O:42])[NH:40][C:38](=[O:39])[N:37]([CH3:43])[CH:36]=3)[C@H:32]([OH:44])[C@@H:31]2[OH:45])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1.[Si:48](Cl)([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49]>C1COCC1.[N+]([O-])([O-])=O.[Ag+]>[CH3:7][O:8][C:9]1[CH:47]=[CH:46][C:12]([C:13]([O:28][CH2:29][C@H:30]2[O:34][C@@H:33]([C:35]3[C:41](=[O:42])[NH:40][C:38](=[O:39])[N:37]([CH3:43])[CH:36]=3)[C@H:32]([O:44][Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49])[C@@H:31]2[OH:45])([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1.[CH3:7][O:8][C:9]1[CH:47]=[CH:46][C:12]([C:13]([O:28][CH2:29][C@H:30]2[O:34][C@@H:33]([C:35]3[C:41](=[O:42])[NH:40][C:38](=[O:39])[N:37]([CH3:43])[CH:36]=3)[C@H:32]([OH:44])[C@@H:31]2[O:45][Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49])([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 67259493HCID 67259493, compound

Product 2

HCID 67259612HCID 67259612, compoundYield 25%HCID 67259754HCID 67259754, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Anhydrous pyridine (3.64 mL) was added to a solution of 5′-O-(4,4′-dimethoxitrityl)-1-N-methylpseudouridine (2.67 g, 4.48 mmol) and AgNO3 (934 mg, 5.69 mmol) in dry THF (32 mL) and stirred at room temperature for 20 min under an argon atmosphere. Followed by addition of tert-butyldimethylsilyl chloride (934 mg, 5.87 mmol) in dry THF (3 mL) and stirred at the same temperature for 3-4 h. The solids were filtered off and the filtrate was concentrated to a crude residue which was applied to a column of silica gel which was saturated with 2% triethylamine in hexanes, and eluted with hexane-ethyl acetate (1:1) to give a pure title compound (780 mg, 25%), and 5′-O-(4,4′-dimethoxitrityl)-3′-O-(tert-butyldimethylsilyl)-1-methylpseudouridine (800 mg, 25%) as amorphous solid.

Workup

  1. stirringstirred at the same temperature for 3-4 h
  2. filtrationThe solids were filtered off
  3. concentrationthe filtrate was concentrated to a crude residue which
  4. washeluted with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-66e12ebbf0fa48f3857a3bf9829c2d9c
Source dataset
uspto-grants-2009_08
Patent number
US07579451B2

Reaction notes

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