Ethyl Acetate → (3-Amino-5-methyl-pyrazin-2-yl)-phenyl-methanone

HRID 2387222Notes

Reaction equation

CON(C)[C:4]([C:6]1[C:11]([NH2:12])=[N:10][C:9]([CH3:13])=[CH:8][N:7]=1)=[O:5].[C:15]1([Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])(O)=O.[Na+].CCOC(C)=O>C1COCC1>[NH2:12][C:11]1[C:6]([C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:5])=[N:7][CH:8]=[C:9]([CH3:13])[N:10]=1

Participants

Conditions

Temperature: -78 °C

Procedure

3-Amino-5-methyl-pyrazin-2-carboylic acid methoxy-methyl-amide (0.3 g, 1.53 mmol) is dissolved in anhydrous THF (30 ml) under N2. The clear yellow solution is cooled to −78° C., and a 1M solution of phenyl magnesium bromide in THF (7.6 ml, 7.6 mmol) is added. The resulting reaction mixture is stirred at −78° C. for 1 hour, and is then allowed to warm to room temperature and stirred for a further 2.5 hours. The reaction mixture is poured onto aq. NaHCO3 and EtOAc. The phases are separated and the aqueous layer is washed with EtOAc. The combined organic layers are washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography (SiO2, 0-7% MeOH in DCM) yields (3-amino-5-methyl-pyrazin-2-yl)-phenyl-methanone as a yellow solid. [M+H]+ 214.

Workup

customThe resulting reaction mixture
temperatureto warm to room temperature
stirringstirred for a further 2.5 hours
customThe phases are separated
washthe aqueous layer is washed with EtOAc
washThe combined organic layers are washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customPurification by flash chromatography (SiO2, 0-7% MeOH in DCM)

Sources & evidence

ORD record: ord-218faaeca2ef45c4b9c74c61bd0ccd10
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268834B2

Reaction notes

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