Water → HCID 86681070, compound
Reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:9]=[N:10][N:11]([CH3:13])[CH:12]=2)=[N:6][CH:5]=[CH:4][N:3]=1.[OH2:14].[OH-].[K+]>CS(C)=O>[CH3:13][N:11]1[CH:12]=[C:8]([C:7]2[C:2](=[O:14])[NH:3][CH:4]=[CH:5][N:6]=2)[CH:9]=[N:10]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To 2-chloro-3-(1-methyl-1H-pyrazol-4-yl)pyrazine (200 mg, 1.03 mmol) from Step 1 of this Example in DMSO (1.5 mL) and water (1.5 mL) was added KOH (890 mg, 15.4 mmol) and the mixture was heated at 80° C. for 3 h. The mixture was cooled and partitioned between EtOAc and 4 N HCl. The aqueous layer was concentrated under reduced pressure and then a mixture of MeOH and EtOH was added and the suspension was filtered through Celite. The filtrate was concentrated under reduced pressure and then Et2O was added and the mixture again concentrated under reduced pressure. The residue was triturated with DCM and filtered to afford crude 3-(1-methyl-1H-pyrazol-4-yl)pyrazin-2(1H)-one (300 mg, quantitative) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 8.60 (s, 1H), 8.18 (s, 1H), 7.24-7.39 (m, 2H), 3.91 (s, 3H).
Workup
- temperatureThe mixture was cooled
- custompartitioned between EtOAc and 4 N HCl
- concentrationThe aqueous layer was concentrated under reduced pressure
- additiona mixture of MeOH and EtOH
- additionwas added
- filtrationthe suspension was filtered through Celite
- concentrationThe filtrate was concentrated under reduced pressure
- additionEt2O was added
- concentrationthe mixture again concentrated under reduced pressure
- customThe residue was triturated with DCM
- filtrationfiltered
Sources & evidence
- ORD record
- ord-2dc3b24fc4b6459cb86f5c90bf02e2f2
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952058B2
Reaction notes
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