Carbon Dioxide → Lithium 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate

HRID 459443Notes

Reaction equation

HRID 459443 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2[N:8]=[CH:9][S:10][C:4]=2[CH2:3]1.[C:11](=[O:13])=[O:12].C([Li:18])CCC>O1CCCC1>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2[N:8]=[C:9]([C:11]([O-:13])=[O:12])[S:10][C:4]=2[CH2:3]1.[Li+:18]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 111864405-Methyl-4,5,6,7-tetrahydrothiazolo(5,4-c)pyridineHCID 178418339Butyllithium

Product 1

HCID 23704331Lithium 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine (6.43 g) was dissolved in absolute tetrahydrofuran (200 ml), to the solution n-butyllithium (1.47N hexane solution, 34.0 ml) was added dropwise at −78° C., and the resultant mixture was stirred for 40 minutes. After carbon dioxide gas was blown into the reaction mixture at −78° C. for 1 hour, the reaction mixture was warmed to room temperature and then concentrated under reduced pressure to obtain the title compound (9.42 g) as pale brown foamy solids.

Workup

  1. additionwas added dropwise at −78° C.
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3a9daf06d1de4b20bc9440aa7fab1960
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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