Pyridine → N2-Isobutyryl-2'-O-Methyl-guanosine

HRID 2119782Notes

Reaction equation

HRID 2119782 reaction equation
C([CH:5]([OH:35])[C@H:6]1[O:10][C@@H:9]([N:11]2[C:26]3[C:14]([C:15]([N:17]=[C:18]([N:25]=3)[NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])=[O:16])=[N:13][C:12]2=[SiH2])[C@H:8]([O:28][CH3:29])[C@@H:7]1[O:30]C(C)(C)C)(C)(C)C.N1C=CC=CC=1.N1C=CC=CC=1.F>ClCCl>[CH3:29][O:28][C@@H:8]1[C@H:7]([OH:30])[C@@H:6]([CH2:5][OH:35])[O:10][C@H:9]1[N:11]1[C:26]2[N:25]=[C:18]([NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[NH:17][C:15](=[O:16])[C:14]=2[N:13]=[CH:12]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 64774Pyridine, hydrofluoride (1:1)HCID 131724333HCID 131724333, compound

Product 1

HCID 135536008N2-Isobutyryl-2'-O-Methyl-guanosineYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (66) (0.51 g, 1 mmol) in anhydrous dichloromethane (5 ml) was added pyridine (0.5 ml) followed by hydrogen fluoride—pyridine (38.5 M, 0.1 ml). After 15 min the solvent was removed in vacuo. Flash chromatography using a gradient of 5-10% methanol in dichloromethane afforded (67) as white foam, 0.34 g, 93% yield.

Workup

  1. customAfter 15 min the solvent was removed in vacuo

Sources & evidence

ORD record
ord-2a2dc6be088f45449c0e37d11d37a52c
Source dataset
uspto-grants-2004_02
Patent number
US06686463B2

Reaction notes

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