Citric Acid → (3-Amino-6-iodo-pyrazin-2-yl)-phenyl-methanone

HRID 272056Notes

Reaction equation

CON(C)[C:4]([C:6]1[C:11]([NH2:12])=[N:10][CH:9]=[C:8]([I:13])[N:7]=1)=[O:5].[C:15]1([Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CCOCC.O.ClCCl>[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][C:8]([I:13])=[CH:9][N:10]=1

Participants

Conditions

Temperature: 55 °C

Procedure

8.00 g (25.97 mmol) of 3-amino-6-iodo-pyrazine-2-carboxylic acid methoxy-methyl-amide was dissolved in 100 ml of anhydrous THF under nitrogen. The solution was cooled to 55° C. and 27 ml of a 3 M solution of phenylmagnesium bromide in ether was added. The mixture was allowed to warm to 10° C. and a solution of 10% citric acid in water was added. The mixture was diluted with dichloromethane and the phases were separated. The aqueous phase was extracted three times with dichloromethane and the combined organic phases were dried over sodium sulfate and evaporated. The resulting solid was crystallized from ethanol to afford 5.74 g (17.66 mmol; 68%) of (3-amino-6-iodo-pyrazin-2-yl)-phenyl-methanone as yellow-orange crystals. 1H-NMR (d6-DMSO) δ: 8.52 [1H] s, 7.94 [2H] s,br, 7.85 [2H] d, 7.62 [1H] t, 7.52 [2H] t. MS: m/z 326 [MH+].

Workup

temperatureto warm to 10° C.
customthe phases were separated
extractionThe aqueous phase was extracted three times with dichloromethane
dry with materialthe combined organic phases were dried over sodium sulfate
customevaporated
customThe resulting solid was crystallized from ethanol

Sources & evidence

ORD record: ord-156e8396442d4655808ff938c142d10f
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452993B2

Reaction notes

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