Tetrahydrofuran → (S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-ol

HRID 388094Notes

Reaction equation

HRID 388094 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[N:8]([C@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH3:13])[C:9](=[O:11])[NH:10][C:5]2=[N:4][CH:3]=1.BrC1N=C(N[C@H:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:29])C(N)=NC=1.[C:37](N1C=CN=C1)([N:39]1C=CN=C1)=O.O1CCC[CH2:50]1>CO>[CH3:50][N:10]1[C:5]2=[N:4][CH:3]=[C:2]([C:35]3[CH:34]=[CH:33][CH:32]=[C:31]4[C:30]=3[CH:28]=[CH:29][CH:37]=[N:39]4)[N:7]=[C:6]2[N:8]([C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[C:9]1=[O:11].[Br:1][C:2]1[N:7]=[C:6]2[N:8]([C@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH3:13])[C:9](=[O:11])[NH:10][C:5]2=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 24815573(S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-olHCID 57880841HCID 57880841, compound

Product 2

HCID 24815573(S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-olYield 62%HCID 66699676(S)-1-Methyl-3-(1-phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-6-Bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. The title compound was prepared using (S)-6-bromo-N2-(1-phenylethyl)pyrazine-2,3-diamine (See Example 3.A) (0.50 g, 1.71 mmol), 1,1′-carbonyldiimidazole (0.35 g, 2.13 mmol), and tetrahydrofuran (7 mL) as described in General Procedure D1. The crude material was dissolved in methanol (5 mL), and the product was triturated with H2O while sonicating. The resulting precipitate was filtered and dried in a vacuum oven overnight to afford 0.34 g (1.07 mmol, 62%) of (S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. MS (ESI) m/z 319.4 [M+1]+.

Workup

  1. customthe product was triturated with H2O
  2. customwhile sonicating
  3. filtrationThe resulting precipitate was filtered
  4. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-c5b65e77832c40acb870a62bbb8e16f1
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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