Pyridine → 7-(2-Thienyl)-3-(beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

HRID 1662298Notes

Reaction equation

HRID 1662298 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[N:12]([C@@H:15]3[O:23][C@H:22]([CH2:24][OH:25])[C@@H:17]([O:18]C(=O)C)[CH2:16]3)[CH:13]=[N:14][C:7]=12.N1C=CC=CC=1.C(N(C(C)C)CC)(C)C.P(N)(OCl)[O:42]N(C(C)C)C(CCC#N)(C)C>C(OCC)(=O)C.CO.C1COCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[N:12]([C@@H:15]3[O:23][C@H:22]([CH2:24][OH:25])[C@@H:17]([OH:18])[C@H:16]3[OH:42])[CH:13]=[N:14][C:7]=12

Participants

8

Reactant 4

HCID 1049PyridineHCID 81531DiisopropylethylamineHCID 674285847-(2-Thienyl)-3-(2-deoxy-3-O-acetyl-beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridineHCID 866390152-cyanoethyl-N,N-diisopropylamino chloro phosphoroamidite

Product 1

HCID 444333047-(2-Thienyl)-3-(beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridineYield 220.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 9 (290 mg, 0.47 mmol) was azeotroped with pyridine, followed by addition of THF (2.4 ml) and diisopropylethylamine (123 μl, 0.7 mmol). To this solution, 2-cyanoethyl-N,N-diisopropylamino chloro phosphoroamidite (115 μl, 0.52 mmol) was added and stirred at room temperature for 1 hour. After addition of methanol (50 μl), the reaction mixture was diluted with ethyl acetate:triethylaime (20:1, v/v) and partitioned with 5% aqueous NaHCO3. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, concentrated and then purified on a silica gel column to give Compound 11 (345 mg, 90%).

Workup

  1. customtriethylaime (20:1, v/v) and partitioned with 5% aqueous NaHCO3
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. custompurified on a silica gel column

Sources & evidence

ORD record
ord-0e5ec37b177a422f87b6c26fd1176234
Source dataset
uspto-grants-2011_10
Patent number
US08030478B2

Reaction notes

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