Sodium Carbonate → 2-Methylthiazolo[5,4-b]pyridine

HRID 2259520Notes

Reaction equation

HRID 2259520 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].C([O-])([O-])=O.[Na+].[Na+].[C:21]([NH:24][C:25]1[C:26](Cl)=[N:27][CH:28]=[CH:29][CH:30]=1)(=O)[CH3:22].[OH-].[Na+]>C1COCC1>[CH3:22][C:21]1[S:2][C:26]2[C:25]([N:24]=1)=[CH:30][CH:29]=[CH:28][N:27]=2

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 4338791N-(2-chloropyridin-3-yl)acetamide

Product 1

HCID 6407272-Methylthiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Phosphorus pentasulfide (56.5 g) and Na2CO3 (13.7 g) were mixed together in 400 mL of THF for ~30 min. To this solution, a solution of the product of Step 1 (17.32 g) in 100 mL of THF was added and the mixture was stirred at room temperature overnight. 2M NaOH (500 mL) was added and the mixture was stirred at room temperature for 2 hr. The product was extracted in EtOAc, washed with brine, dried over Na2SO4, and purified by flash chromatography on silica with EtOAc: toluene 20:80; yield: 12.07 g, (83%).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. extractionThe product was extracted in EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. custompurified by flash chromatography on silica with EtOAc: toluene 20:80

Sources & evidence

ORD record
ord-4f7276a965f24679ae00e039e90563e7
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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