Potassium Carbonate → HCID 86601382, compound

HRID 852932Notes

Reaction equation

HRID 852932 reaction equation
[H-].[Na+].O[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[H][H].[C:12]([O-:15])([O-])=O.[K+].[K+].Br.[NH2:19][C:20]1[S:21]C(Br)=[CH:23][N:24]=1>COCCOC>[N:5]1[CH:6]=[CH:7][CH:8]=[C:9]([O:15][C:12]2[S:21][C:20]([NH2:19])=[N:24][CH:23]=2)[CH:4]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 27238485-Bromothiazol-2-amine monohydrobromideHCID 178418361HCID 178418361, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 86601382HCID 86601382, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of (NaH 60% in mineral oil, 169 mg, 4.23 mmol) in DME (10 mL) was added 2-hydroxypyridine (366 mg, 3.85 mmol). [Hydrogen evolution was observed]. Then, powdered K2CO3 (2.31 g, 19.2 mmol) was added followed by portion-wise addition of 2-amino-5-bromothiazole hydrobromide (1.00 g, 3.85 mmol). The mixture was refluxed with stirring for 16 h and allowed to cool down to room temperature, quenched with water and partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc and organic phase was extracted with HCl 1N. The acidic extract was neutralized with saturated NaHCO3 and the precipitate was extracted first with EtOAc and then with a mixture of MeOH/CHCl3 (20:85). The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was crystallized by addition of a mixture of MeOH/CHCl3 (5:95) affording the title compound 170 (21 mg, 3%). 1H NMR: (CD3OD) δ (ppm): 9.05 (dd, J=7.2, 2.0 Hz, 1H), 8.70 (ddd, J=9.2, 6.7, 2.2 Hz, 1H), 8.44 (s, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.59 (bs, 2H), 7.58 (td, J=6.8, 1.4 Hz, 1H). m/z: 194.2 (MH+).

Workup

  1. temperatureThe mixture was refluxed
  2. customquenched with water
  3. custompartitioned between water and EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc and organic phase
  5. extractionwas extracted with HCl 1N
  6. extractionThe acidic extract
  7. extractionthe precipitate was extracted first with EtOAc
  8. additionwith a mixture of MeOH/CHCl3 (20:85)
  9. dry with materialThe combined organic extracts were dried over MgSO4
  10. concentrationconcentrated in vacuo
  11. customThe residue was crystallized by addition of a mixture of MeOH/CHCl3 (5:95)

Sources & evidence

ORD record
ord-4a81445fd6344130a1444bd2aa50ec93
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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