Sodium Bicarbonate → HCID 68684762, compound

HRID 2238678Notes

Reaction equation

HRID 2238678 reaction equation
O[CH2:2][C:3]1[C:4]2[N:5]([C:9]([C:12]3[C:17]([C:18]#[N:19])=[CH:16][N:15]=[C:14]([S:20][CH3:21])[N:13]=3)=[CH:10][N:11]=2)[CH:6]=[CH:7][CH:8]=1.COCCN(S(F)(F)[F:32])CCOC.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[F:32][CH2:2][C:3]1[C:4]2[N:5]([C:9]([C:12]3[C:17]([C:18]#[N:19])=[CH:16][N:15]=[C:14]([S:20][CH3:21])[N:13]=3)=[CH:10][N:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluoride2×HCID 68685025HCID 68685025, compound

Product 1

HCID 68684762HCID 68684762, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-40 °C

Procedure

4.23 g of the 4-[8-(hydroxymethyl)imidazo[1,2-a]pyridin-3-yl]-2-(methylthio)pyrimidine-5-carbonitrile [147-2] was dissolved in 500 mL of chloroform, then 5.2 mL of bis-(2-methoxyethyl)aminosulfur trifluoride was added thereto at −40° C., and stirred at the same temperature for 1 hour. 2.6 mL of bis-(2-methoxyethyl)aminosulfur trifluoride was further added, and stirred at the same temperature for 1 hour. Thereto, a saturated aqueous solution of sodium hydrogen carbonate was slowly added, and the mixture was extracted with chloroform. The organic layer was washed with water and saturated brine in the subsequent order, and dried over anhydrous magnesium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the thus obtained residue was dissolved in a small amount of chloroform and solidified by adding diethyl ether, to obtain 3.43 g of 4-[8-(fluoromethyl)imidazo[1,2-a]pyridin-3-yl]-2-(methylthio)pyrimidine-5-carbonitrile [147-3] as a light brown solid.

Workup

  1. stirringstirred at the same temperature for 1 hour
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with water and saturated brine in the subsequent order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insolubles were filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. dissolutionthe thus obtained residue was dissolved in a small amount of chloroform
  8. additionby adding diethyl ether

Sources & evidence

ORD record
ord-9d95811cc6fa4acd992af571169b4894
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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