Pyridine → HCID 68502799, compound

HRID 501883Notes

Reaction equation

HRID 501883 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][C:9]1[CH:55]=[CH:54][C:12]([C:13]([O:28][CH2:29][C@H:30]2[O:34][C@@H:33]([N:35]3[CH:50]=[C:49]([CH3:51])[C:39]([NH:40][C:41](=[O:48])[C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)=[N:38][C:36]3=[O:37])[C@H:32]([OH:52])[C@@H:31]2[OH:53])([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:56](Cl)([C:59]([CH3:62])([CH3:61])[CH3:60])([CH3:58])[CH3:57]>C1COCC1.[N+]([O-])([O-])=O.[Ag+]>[CH3:7][O:8][C:9]1[CH:55]=[CH:54][C:12]([C:13]([O:28][CH2:29][C@H:30]2[O:34][C@@H:33]([N:35]3[CH:50]=[C:49]([CH3:51])[C:39]([NH:40][C:41](=[O:48])[C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=4)=[N:38][C:36]3=[O:37])[C@H:32]([O:52][Si:56]([C:59]([CH3:62])([CH3:61])[CH3:60])([CH3:58])[CH3:57])[C@@H:31]2[OH:53])([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 68500841HCID 68500841, compound

Product 1

HCID 68502799HCID 68502799, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Anhydrous pyridine (3.6 mL) was added to a solution of 5′-O-(4,4′-dimethoxitrityl)-N-benzoyl-5-methylcytidine (7.06 g, 10.64 mmol) and AgNO3 (2.17 g, 12.75 mmol) in dry THF (71 mL) and stirred at room temperature for 20 min under an argon atmosphere. Followed by addition of tert-butyldimethylsilyl chloride (1.89 g, 12.81 mmol) in dry THF (6 mL) and stirred at the same temperature for 2-3 h. The solids were filtered off and the filtrate was concentrated to a crude residue which was applied to a column of silica gel eluted with hexane-ethyl acetate (3:1) to give a pure title compound (3.04 g, 37%), and a mixture of 2′- and 3′-isomers (3.04 g) as amorphous solid. 1H-NMR (DMSO-d6, 400 MHz): δ 12.96 (br, 1H), 8.20-7.81 (m, 2H, ArH), 7.82 (s, 1H), 7.58-7.22 (m, 12H, ArH), 6.92-6.90 (m, 4H, ArH), 5.80 (d, 1H, J=3.6 Hz, H-1′), 5.20 (d, 1H, J=6.4 Hz, 3′-OH), 4.32 (dd, 1H, H-2′), 4.16-4.13 (dd, 1H, H-3′), 4.08 (m, 1H, H-4′), 3.78 (s, 6H, 2OCH3), 3.38-3.25 (m, 2H, H-5′), 1.80 (s, 3H, 5-CH3), 0.86 (s, 9H, t-Bu), 0.08 (s, 6H, 2 CH3).

Workup

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

Sources & evidence

ORD record
ord-dba94fd7e67d495aab58656177b6b27f
Source dataset
uspto-grants-2010_08
Patent number
US07772387B2

Reaction notes

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