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

HRID 546394Notes

Reaction equation

HRID 546394 reaction equation
Br[C:2]1[S:3][C:4]2[CH2:5][N:6]([CH3:11])[CH2:7][CH2:8][C:9]=2[N:10]=1.C([Li:16])CCC.[C:17](=[O:19])=[O:18]>C(OCC)C>[CH3:11][N:6]1[CH2:7][CH2:8][C:9]2[N:10]=[C:2]([C:17]([O-:19])=[O:18])[S:3][C:4]=2[CH2:5]1.[Li+:16]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 111723352-Bromo-5-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 3283Diethyl EtherSolvent

Procedure

2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo-[5,4-c]pyridine (531 mg) was dissolved in absolute diethyl ether (20 ml), n-butyllithium (1.54N hexane solution, 1.63 ml) was added dropwise at −78° C., and the mixture was stirred for 30 minutes with ice cooling. After passing carbon dioxide into the reaction mixture at −78° C. for 1 hour, the mixture was warmed to room temperature. The reaction mixture was concentrated under reduced pressure to obtain the title compound (523 mg) as a pale brown solid.

Workup

  1. customat −78° C.
  2. customfor 1 hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-de51864ea3794d6f9b356a513dd61879
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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