HCID 178469223, compound → HCID 178470320, compound

HRID 1930110Notes

Reaction equation

[OH:1][C:2]1[CH:3]([CH3:14])[NH:4][C:5]([CH3:13])=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1>C(Cl)Cl.CCOC(C)=O.CCCC(C)C.[O-2].[O-2].[Mn+4]>[OH:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([CH3:13])=[N:4][C:3]=1[CH3:14]

Participants

Conditions

Temperature: 35 °C

Procedure

Manganese dioxide (150 g) was added to a suspension of ethyl 6-hydroxy-3,5-dimethyl-4,5-dihydropyrazine-2-carboxylate (121 g, 610.44 mmol) in DCM (1.8 L) at ambient temperature giving rise to a 2° C. exotherm. The reaction was stirred for 10 minutes then warmed to 35° C. for 1 hour. The reaction was incomplete so an additional 115 g of Manganese dioxide was added and the reaction stirred for 1 hour at 35° C. then stirred to cool to ambient temperature. The reaction was filtered through a short bed of silica and washed through with 2 L of 1:1 EtOAc/iso-hexane and finally 2×2 L EtOAc. The fractions were then combined and reduce in-vacuo to give an orange solid, which was slurried in 300 mL of 1:1 EtOAc/iso-hexane, filtered and washed with iso-hexane to afford the title compound (87 g, 72.6%) as an orange solid.

Workup

customgiving rise to a 2° C. exotherm
additionwas added
stirringthe reaction stirred for 1 hour at 35° C.
stirringthen stirred
temperatureto cool to ambient temperature
filtrationThe reaction was filtered through a short bed of silica
washwashed through with 2 L of 1:1 EtOAc/iso-hexane and finally 2×2 L EtOAc
customto give an orange solid, which
filtrationfiltered
washwashed with iso-hexane

Sources & evidence

ORD record: ord-2c76a43e95e74bd2855f9e1169e7bc54
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188092B2

Reaction notes

Loading…