Trimethylsilyl triflate → HCID 137108748, compound

HRID 60773Notes

Reaction equation

HRID 60773 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:12])[C:5]2[S:10][C:9](=[O:11])[NH:8][C:6]=2[N:7]=1.[CH3:13][CH:14]([CH3:34])[C:15]([O:17][C@H:18]([C@@H:21]1[CH2:25][C@@H:24]([O:26][C:27](=[O:29])[CH3:28])[C@@H:23](OC(=O)C)[O:22]1)[CH2:19][CH3:20])=[O:16].[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C>C(#N)C>[CH3:34][CH:14]([CH3:13])[C:15]([O:17][C@H:18]([C@@H:21]1[CH2:25][C@@H:24]([O:26][C:27](=[O:29])[CH3:28])[C@H:23]([N:8]2[C:6]3[N:7]=[C:2]([NH2:1])[NH:3][C:4](=[O:12])[C:5]=3[S:10][C:9]2=[O:11])[O:22]1)[CH2:19][CH3:20])=[O:16]

Participants

5

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 121396294[(1S)-1-[(2S,4R,5R)-4,5-diacetoxytetrahydrofuran-2-yl]propyl] 2-methylpropanoate2×HCID 1357436395-Aminothiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione

Product 1

HCID 137108748HCID 137108748, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 5-amino-3,6-dihydrothiazolo[4,5-d]pyrimidine-2,7-dione (63 mg, 0.34 mmol) in ACN (5 mL) was added BSA (252 μL, 1.02 mmol). The resulting reaction mixture was then stirred at 70° C. under argon for 0.5 hour to form a clear solution. After the solution was cooled to room temperature, [(1S)-1-[(2S,4R,5R)-4,5-diacetoxytetrahydrofuran-2-yl]propyl] 2-methylpropanoate (compound 42b, 105 mg, 0.34 mmol) and TMSOTf (113 μL, 0.51 mmol) were added in sequence. After being heated with stirring at 70° C. for 14 hours, the resulting mixture was concentrated in vacuo to remove the solvent and the residue was purified by column chromatography on silica gel (eluting with 0-5% methanol in DCM) to afford 75 mg of [(1S)-1-[(2S,4R,5R)-4-acetoxy-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-2-yl]propyl] 2-methylpropanoate (compound 42c) as a light yellow solid.

Workup

  1. additionwas added BSA (252 μL, 1.02 mmol)
  2. customThe resulting reaction mixture
  3. customto form a clear solution
  4. temperatureAfter the solution was cooled to room temperature
  5. temperatureAfter being heated
  6. stirringwith stirring at 70° C. for 14 hours
  7. concentrationthe resulting mixture was concentrated in vacuo
  8. customto remove the solvent
  9. customthe residue was purified by column chromatography on silica gel (eluting with 0-5% methanol in DCM)

Sources & evidence

ORD record
ord-1099e4f4df684fb7969c46eb81503d31
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

Loading…