Hydrochloric Acid → HCID 46916374, compound

HRID 1396697Notes

Reaction equation

HRID 1396697 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]([NH2:19])[N:13]=[C:14](SC)[C:15]=3[N:16]=2)=[CH:4][CH:3]=1.Cl.[CH3:21][O:22][CH2:23][CH2:24][OH:25]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[N:11]=[C:12]([NH2:19])[N:13]=[C:14]([O:25][CH2:24][CH2:23][O:22][CH3:21])[C:15]=3[N:16]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 80192-MethoxyethanolHCID 50941766HCID 50941766, compound

Product 1

HCID 46916374HCID 46916374, compoundYield 80%

Conditions

Temperature
80 °C

Procedure

To a solution of Na (2.0 mg, 0.07 mmol) in 2-methoxyethanol (1 ml) was added 2-(4-fluorophenyl)-7-methylthio-thiazolo[5,4-d]pyrimidin-5-amine (40 mg, 0.14 mmol). The reaction mixture was heated at 80° C. for 20 hours. After cooling, the mixture was neutralized with 1N HCl and the solvent was removed under reduced pressure. The crude residue was extracted by ethyl acetate, brine and dried over Na2SO4. After removing the solvents under reduced pressure, the residue was purified by flash chromatography on silica (CH2Cl2/MeOH 100:1) to yield the title compound as a white solid (35 mg, 80%).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed under reduced pressure
  3. extractionThe crude residue was extracted by ethyl acetate, brine
  4. dry with materialdried over Na2SO4
  5. customAfter removing the solvents under reduced pressure
  6. customthe residue was purified by flash chromatography on silica (CH2Cl2/MeOH 100:1)

Sources & evidence

ORD record
ord-df1faad62a8346169d108594056e174b
Source dataset
uspto-grants-2014_12
Patent number
US08901132B2

Reaction notes

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