Acetonitrile → HCID 67975786, compound

HRID 2046174Notes

Reaction equation

HRID 2046174 reaction equation
[O:1]([CH2:8][C:9]1[CH:18]=[C:12]2[C:13](=[O:17])[NH:14][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(#N)C>C1(C)C=CC=CC=1.O.[O-2].[O-2].[Mn+4]>[NH4+:10].[OH-:1].[O:1]([CH2:8][C:9]1[CH:18]=[C:12]2[C:13](=[O:17])[NH:14][CH:15]=[CH:16][N:11]2[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 6342Acetonitrile2×HCID 57411799HCID 57411799, compound

Product 2

HCID 14923Ammonium HydroxideHCID 67975786HCID 67975786, compoundYield 9.5%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Manganese dioxide (0.36 g, 4.1 mmol) was added to a stirred solution of 2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (0.10 g, 0.41 mmol) in toluene (5 mL). The mixture was stirred at 120° C. for 10 hours and then filtered through a pad of diatomaceous earth and washed with MeOH and AcOEt. The solvents were evaporated in vacuo and the crude product purified by RP HPLC on (C18 XBridge 30×100 5 um). Mobile phase (Gradient from 80% 0.1% NH4CO3H/NH4OH pH 9 solution in H2O, 20% ACN to 0% 0.1% NH4CO3H/NH4OH pH 9 solution in H2O, 100% ACN) to yield 2-phenoxymethyl-5H-pyrazolo[1,5-a]pyrazin-4-one (4.71 mg, 4.6% yield) as a solid.

Workup

  1. filtrationfiltered through a pad of diatomaceous earth
  2. washwashed with MeOH and AcOEt
  3. customThe solvents were evaporated in vacuo
  4. customthe crude product purified by RP HPLC on (C18 XBridge 30×100 5 um)

Sources & evidence

ORD record
ord-baf12de10fde4aa49b93def61bcb9407
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

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