Ammonium formate → 4,5,6,7-Tetrahydro-2-(phenoxymethyl)-pyrazolo[1,5-a]pyrazine

HRID 2369582Notes

Reaction equation

[O:1]([CH2:8][C:9]1[CH:24]=[C:12]2[CH2:13][N:14](CC3C=CC=CC=3)[CH2:15][CH2:16][N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>[Pd].CO>[O:1]([CH2:8][C:9]1[CH:24]=[C:12]2[CH2:13][NH:14][CH2:15][CH2:16][N:11]2[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

10% Palladium on charcoal (0.21 g, 0.2 mmol) was added to a stirred suspension of 4,5,6,7-tetrahydro-2-(phenoxymethyl)-5-(phenylmethyl)-pyrazolo[1,5-a]pyrazine (0.65 g, 2.0 mmol) and ammonium formate (0.38 g, 6.1 mmol) in MeOH (14 mL) in a sealed tube under N2. The mixture was stirred at 90° C. for 1 hour, filtered through a pad of diatomaceous earth and washed with DCM. The solvents were evaporated in vacuo to yield 4,5,6,7-tetrahydro-2-(phenoxymethyl)-pyrazolo[1,5-a]pyrazine (0.58 g, 66% yield) as a clear oil that was used in the next step without further purification. C13H15N3O LCMS: Rt 1.19, m/z 230 [M+H]+ (see LCMS Method 1).

Workup

filtrationfiltered through a pad of diatomaceous earth
washwashed with DCM
customThe solvents were evaporated in vacuo

Sources & evidence

ORD record: ord-e5d942450b7646d384203a33f77e43da
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703946B2

Reaction notes

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