Hydrochloric Acid → HCID 66758658, compound

HRID 718243Notes

Reaction equation

HRID 718243 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-e602a408636c4b1e8f8f1008e6da4e7d
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

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