1,1'-Carbonyldiimidazole → HCID 74324247, compound

HRID 1821644Notes

Reaction equation

HRID 1821644 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([NH:9][CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:11])[C:5]([NH2:8])=[N:6][CH:7]=1.N1([C:23](N2C=CN=C2)=[O:24])C=CN=C1>O1CCCC1>[Br:1][C:2]1[N:3]=[C:4]2[N:9]([CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH3:11])[C:23](=[O:24])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 76723649HCID 76723649, compound

Product 1

HCID 74324247HCID 74324247, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-N3-(1-phenylethyl)pyrazine-2,3-diamine (1.77 g, 6.04 mmol) in anhydrous tetrahydrofuran (30 mL) was added diimidazol-1-ylmethanone (1.47 g, 9.06 mmol) at room temperature. After stirring for 20 h, the reaction was concentrated under reduced pressure. Purification of the resultant residue by flash chromatography [silica gel; hexanes/ethyl acetate (2:1)] afforded 6-bromo-1-(1-phenylethyl)-1,3-dihydroimidazo[4,5-b]pyrazin-2-one as a red brown solid (1.64 g, 85%). 1H NMR (300 MHz, DMSO): δ 12.31 (s, 1H), 8.04 (s, 1H), 7.40-7.27 (m, 5H), 5.61 (q, J=7.2 Hz, 1H), 1.90 (d, J=7.2 Hz, 3H).

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. customPurification of the resultant residue by flash chromatography [silica gel; hexanes/ethyl acetate (2:1)]

Sources & evidence

ORD record
ord-0511d3326d1140c08a4d3da0555e9ce1
Source dataset
uspto-grants-2009_10
Patent number
US07608622B2

Reaction notes

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