Hydrochloric Acid → HCID 67976039, compound

HRID 2046190Notes

Reaction equation

HRID 2046190 reaction equation
Cl[Si:2]([CH3:5])([CH3:4])[CH3:3].[OH:6][CH2:7][C@@H:8]1[CH2:13][N:12]2[N:14]=[C:15]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:16]=[C:11]2[C:10](=[O:25])[NH:9]1.Cl>C(#N)C>[O:18]([CH2:17][C:15]1[CH:16]=[C:11]2[C:10](=[O:25])[NH:9][C@H:8]([CH2:7][O:6][Si:2]([CH3:5])([CH3:4])[CH3:3])[CH2:13][N:12]2[N:14]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 67974237(S)-6-hydroxymethyl-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one

Product 1

HCID 67976039HCID 67976039, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Chlorotrimethylsilane (0.30 mL, 2.41 mmol) was added to a solution of (S)-6-hydroxymethyl-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (0.33 g, 2.4 mmol) and TEA (0.33 mL, 2.4 mmol) in ACN (6 mL) at 0° C. The reaction was stirred for 30 minutes at room temperature. Then a 1N solution of HCl was added and the mixture extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo to yield (S)-2-phenoxymethyl-6-trimethylsilanyloxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (0.375 g, 90% yield) as an off-white solid that was used in the next step without further purification.

Workup

  1. extractionthe mixture extracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-b7a7132a11be4abba77b4a3b1ebdc587
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

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