Triethylsilane → HCID 178430920, compound

HRID 2209214Notes

Reaction equation

HRID 2209214 reaction equation
C([SiH](CC)CC)C.C([O:15][C:16]1[C:17]2[N:18]([N:23]=[CH:24][C:25]=2[CH2:26]O)[CH:19]=[C:20]([Cl:22])[N:21]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[Cl:22][C:20]1[N:21]=[C:16]([OH:15])[C:17]2[N:18]([N:23]=[CH:24][C:25]=2[CH3:26])[CH:19]=1

Participants

4

Reactant 2

HCID 12052Triethylsilane2×HCID 117842882(4-(Benzyloxy)-6-chloropyrazolo[1,5-a]pyrazin-3-yl)methanol

Product 1

HCID 178430920HCID 178430920, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (0.2 ml, 1.25 mmol) was added slowly to a solution of (4-(benzyloxy)-6-chloropyrazolo[1,5-a]pyrazin-3-yl)methanol 5.51 (142 mg, 0.49 mmol) in TFA (3 mL). After 19 hours, an additional 0.4 mL of triethylsilane was added and mixture was heated to 60 degrees for 4.5 hours. Mixture was cooled to rt and concentrated under reduced pressure. Resulting residue was taken up in DCM and washed with sat. NaHCO3 (aq). Aqueous layer was extracted with DCM. Combined organics were dried, filtered, and concentrated under reduced pressure to yield 6-chloro-3-methylpyrazolo[1,5-a]pyrazin-4-ol 5.52 (90 mg), which was used in the next step without further purification.

Workup

  1. temperaturemixture was heated to 60 degrees for 4.5 hours
  2. concentrationconcentrated under reduced pressure
  3. washwashed with sat. NaHCO3 (aq)
  4. extractionAqueous layer was extracted with DCM
  5. customCombined organics were dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0409d61490a2499c8d39d9dc27132fae
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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