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Methyl 2-oxo-1,2,3,4-tetrahydrothieno[3,2-b]pyrazine-6-carboxylate → Methyl 2-oxo-1,2-dihydrothieno[2,3-b]pyrazine-6-carboxylate

HRID 1184828
Notes
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Reaction equation

HRID 1184828 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[S:10][C:5]=2[NH:4][CH2:3]1>C1COCC1.[O-2].[Mn+4].[O-2].[O-2].[Mn+2]>[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[S:10][C:5]=2[N:4]=[CH:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 67125709Methyl 2-oxo-1,2,3,4-tetrahydrothieno[3,2-b]pyrazine-6-carboxylate

Product 1

HCID 67125557Methyl 2-oxo-1,2-dihydrothieno[2,3-b]pyrazine-6-carboxylateYield 95%

Reagents, catalysts & solvents 3

HCID 160959Manganese oxideCatalystHCID 178418406HCID 178418406, compoundCatalystHCID 8028Tetrahydrofuran
Solvent

Procedure

To a suspension of methyl 2-oxo-1,2,3,4-tetrahydrothieno[3,2-b]pyrazine-6-carboxylate 20 (515 mg, 2.427 mmol) in THF (30 mL) was added manganese(IV) oxide (2.11 g, 24.27 mmol). The reaction was stirred at rt for 30 min. manganese oxide was filtrated and washed with EtOAc. The filtrate was evaporated to give crude methyl 2-oxo-1,2-dihydrothieno[3,2-b]pyrazine-6-carboxylate 21 (483 mg, 95%). NMR (400 MHz, DMSO-d6) 3.90 (s, 3H), 7.62 (br s, 1H), 8.13 (s, 1H), 12.80 (br s, 1H). (m/z)=211 (M+H)+.

Workup

  1. filtrationwas filtrated
  2. washwashed with EtOAc
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-a63983bbf26a4e568c3ebdfeef50c9dc
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08669256B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes