Tetramethyltin → HCID 71268198, compound

HRID 926433Notes

Reaction equation

HRID 926433 reaction equation
C[Sn](C)(C)C.[C@@H:6]1([N:14]2[CH:18]=[C:17](I)[CH:16]=[C:15]2[N+:20]([O-:22])=[O:21])[O:11][C@H:10]([CH2:12][OH:13])[C@@H:8]([OH:9])[CH2:7]1.[C:23]1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[C@@H:6]1([N:14]2[CH:18]=[C:17]([CH3:23])[CH:16]=[C:15]2[N+:20]([O-:22])=[O:21])[O:11][C@H:10]([CH2:12][OH:13])[C@@H:8]([OH:9])[CH2:7]1

Participants

6

Reactant 3

HCID 11661TetramethyltinHCID 11773TriphenylarsineHCID 67428497HCID 67428497, compound

Product 1

HCID 71268198HCID 71268198, compoundYield 150%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Tetramethyltin (287 μL, 2 mmol) was added to a DMF (2 mL) solution containing 1-(2-deoxy-β-D-ribofuranosyl)-4-iodo-2-nitropyrrole (142 mg, 0.4 mmol), bis(triphenylphosphine)palladium(II) dichloride (14 mg, 0.02 mmol), and triphenylarsine (12 mg, 0.04 mmol), followed by reaction at 60° C. for 2 days. The reaction solution was separated between ethyl acetate (50 mL) and water (50 mL). The organic layer was concentrated and purified by HPLC to yield 1-(2-deoxy-β-D-ribofuranosyl)-4-methyl-2-nitropyrrole (15 mg, 0.06 mmol, 15%).

Workup

  1. customfollowed by reaction at 60° C. for 2 days
  2. customThe reaction solution was separated between ethyl acetate (50 mL) and water (50 mL)
  3. concentrationThe organic layer was concentrated
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-cb6c263f2d3a44c9af659b766c45309d
Source dataset
uspto-grants-2016_03
Patent number
US09285319B2

Reaction notes

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