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Water → Methyl 4-(benzyloxy)-6-chloropyrazolo[1,5-a]pyrazine-3-carboxylate

HRID 2209204
Notes
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Reaction equation

HRID 2209204 reaction equation
C(=O)([O-])[O-].[K+].[K+].CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:20][N+:21]1[CH:26]=[C:25]([Cl:27])[N:24]=[C:23]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:22]=1.[C:36]([O:40][CH3:41])(=[O:39])[C:37]#[CH:38].O>CN(C=O)C>[CH2:29]([O:28][C:23]1[C:22]2[N:21]([N:20]=[CH:38][C:37]=2[C:36]([O:40][CH3:41])=[O:39])[CH:26]=[C:25]([Cl:27])[N:24]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13536Methyl propiolateHCID 1178435431-Amino-3-(benzyloxy)-5-chloropyrazin-1-ium 2,4,6-trimethylbenzenesulfonate

Product 1

HCID 117843324Methyl 4-(benzyloxy)-6-chloropyrazolo[1,5-a]pyrazine-3-carboxylateYield 44.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (457 mg, 3.31 mmol) was added to a mixture of 1-amino-3-(benzyloxy)-5-chloropyrazin-1-ium 2,4,6-trimethylbenzenesulfonate 5.34 (992 mg, 2.28 mmol) and methyl propiolate (0.24 mL, 2.66 mmol) in DMF (11 mL) at room temperature. After stifling overnight, reaction mixture was poured into water and extracted with ethyl acetate. Combined organics were washed with 50% brine, dried, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (0-30% ethyl acetate/hexanes) to yield methyl 4-(benzyloxy)-6-chloropyrazolo[1,5-a]pyrazine-3-carboxylate 5.35 (320 mg).

Workup

  1. customreaction mixture
  2. extractionextracted with ethyl acetate
  3. washCombined organics were washed with 50% brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (0-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bc42cc98174149eeb03f16d2cf7452b3
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09376441B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes