Imidazole → 5-Amino-3-(5'-o-tert-butyl-dimethylsilanyl-beta-d-ribofuranosyl)-3h-thiazolo[4,5-d]pyrimidin-2-one

HRID 2102283Notes

Reaction equation

HRID 2102283 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]3[OH:14])[C:6]=2[N:7]=1.N1C=CN=C1.[Si:26](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CN(C=O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:18][C@H:17]([CH2:19][O:20][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[C@@H:15]([OH:16])[C@H:13]3[OH:14])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 101931095-Amino-3-beta-D-ribofuranosyl-3H-thiazolo[4,5-d]pyrimidin-2-one

Product 1

HCID 667077065-Amino-3-(5'-o-tert-butyl-dimethylsilanyl-beta-d-ribofuranosyl)-3h-thiazolo[4,5-d]pyrimidin-2-oneYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 90 (0.68 g, 2.28 mmol) in DMF (10 mL) was added imidazole (0.54 g, 7.93 mmol) and tert-butyldimethylsilyl chloride (0.68 g, 4.56 mmol) sequentially. The reaction mixture was stirred at room temperature for 2 h, at which point it was concentrated and purified by flash column chromatography (silica, MeOH/CHCl3; gradient=5-20%) to afford 0.49 g (52%) 91 as a white solid: 1H (400 MHz, d6-DMSO) δ 8.33 (s, 1H), 6.87 (s, 2H), 5.90 (d, J=4.0 Hz, 1H), 5.33 (d, J=5.6 Hz, 1H), 5.00 (d, J=5.2 Hz, 1H), 4.79 (q, J=5.2 Hz, 1H), 4.16 (q, J=5.2 Hz, 1H), 3.77 (m, 2H), 3.64 (dd, J=12.0, 7.2 Hz, 1H), 0.84 (s, 9H), 0.00 (s, 6H); MS(+)-ES [M+H]+m/z 415.4.

Workup

  1. concentrationwas concentrated
  2. custompurified by flash column chromatography (silica, MeOH/CHCl3; gradient=5-20%)

Sources & evidence

ORD record
ord-cb622f68698e4cc0aecedcf96f9610a5
Source dataset
uspto-grants-2009_08
Patent number
US07576068B2

Reaction notes

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