Hydrochloric Acid → HCID 66758658, compound

HRID 1396712Notes

Reaction equation

HRID 1396712 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[N:11]=[C:12]([S:19][CH3:20])[N:13]=[C:14](SC)[C:15]=3[N:16]=2)=[CH:4][CH:3]=1.Cl.[CH2:22]([OH:24])[CH3:23]>>[CH2:22]([O:24][C:14]1[C:15]2[N:16]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[S:9][C:10]=2[N:11]=[C:12]([S:19][CH3:20])[N:13]=1)[CH3:23]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 66758469HCID 66758469, compound

Product 1

HCID 66758658HCID 66758658, compoundYield 60%

Conditions

Temperature
80 °C

Procedure

To a solution of Na (2.0 mg, 0.08 mmol) in ethanol (1 ml) was added 2-(4-fluorophenyl)-5,7-bis(methylthio)thiazolo[5,4-d]pyrimidine (50 mg, 0.15 mmol). The reaction mixture was heated at 80° C. for 3 hours. After cooling, the mixture was neutralized with 1N HCl and the solvent was removed under reduced pressure. The crude residue was redissolved in ethyl acetate, extracted with brine and dried over Na2SO4. After removing the solvents in vacuo, the residue was purified by flash chromatography on silica (EtOAc/Hex 1:50), yielding the title compound as a white solid (30 mg, 60%).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe crude residue was redissolved in ethyl acetate
  4. extractionextracted with brine
  5. dry with materialdried over Na2SO4
  6. customAfter removing the solvents in vacuo
  7. customthe residue was purified by flash chromatography on silica (EtOAc/Hex 1:50)

Sources & evidence

ORD record
ord-4b026d14457a4d309e1aa057c360df92
Source dataset
uspto-grants-2014_12
Patent number
US08901132B2

Reaction notes

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