Tributyltin Chloride → HCID 68159442, compound

HRID 341026Notes

Reaction equation

HRID 341026 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:10][CH:9]=[N:8][CH:7]=1.C([Li])CCC.C([Sn](Cl)(CCCC)CCCC)CCC.C1(C)C(C([O:38][C@@H:39]2[C@@H:43]([CH2:44][O:45]C(C3C(C)=CC=CC=3)=O)[O:42][C@@H:41]([N:55]3[C:59]4=[N:60][CH:61]=[CH:62][C:63](I)=[C:58]4[CH:57]=[CH:56]3)[CH2:40]2)=O)=CC=CC=1>C(OCC)C.CN(C=O)C>[C@@H:41]1([N:55]2[C:59]3=[N:60][CH:61]=[CH:62][C:63]([C:9]4[S:10][C:6]([C:2]5[S:1][CH:5]=[CH:4][CH:3]=5)=[CH:7][N:8]=4)=[C:58]3[CH:57]=[CH:56]2)[O:42][C@H:43]([CH2:44][OH:45])[C@@H:39]([OH:38])[CH2:40]1

Participants

7

Reactant 4

HCID 15096Tributyltin ChlorideHCID 11217456Thiazole, 5-(2-thienyl)-HCID 131731282HCID 131731282, compoundHCID 178418339Butyllithium

Product 1

HCID 68159442HCID 68159442, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 5-(2-thienyl)thiazole (0.4 mmol) in diethyl ether was cooled to −78° C., and n-butyllithium (0.4 mmol, 1.57 M solution in hexane) was added thereto, followed by stirring at −78° C. for 30 min. Furthermore, tributylstannyl chloride was added thereto, followed by stirring at room temperature for 30 min. The reaction solution was separated between ethyl acetate and water. The organic layer was washed with saturated brine and concentrated, and 1-[2-deoxy-3,5-di-O-(toluoyl)-β-D-ribofuranosyl]-4-iodo-pyrrolo[2,3-b]pyridine (120 mg, 0.2 mmol), chlorobistriphenylphosphine palladium (5% mol), and DMF (2 mL) were added thereto, followed by stirring at 100° C. for 1 hr. The reaction solution was separated between ethyl acetate and water, and the organic layer was washed with saturated brine and water, dried over anhydrous sodium sulfate, and concentrated. After purification with a silica gel column and addition of sodium methoxide (1.6 mL), the resulting mixture was stirred at room temperature for 30 min. dDvas nucleoside (34 mg) was purified with a silica gel column and by HPLC.

Workup

  1. stirringby stirring at room temperature for 30 min
  2. customThe reaction solution was separated between ethyl acetate and water
  3. washThe organic layer was washed with saturated brine
  4. concentrationconcentrated
  5. stirringby stirring at 100° C. for 1 hr
  6. customThe reaction solution was separated between ethyl acetate and water
  7. washthe organic layer was washed with saturated brine and water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customAfter purification
  11. additionwith a silica gel column and addition of sodium methoxide (1.6 mL)
  12. stirringthe resulting mixture was stirred at room temperature for 30 min. dDvas nucleoside (34 mg)
  13. customwas purified with a silica gel column and by HPLC

Sources & evidence

ORD record
ord-fdfcb3c5cd1648acbea3de5be205b063
Source dataset
uspto-grants-2014_11
Patent number
US08895712B2

Reaction notes

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