Methyl iodide → 2,8-Dibenzyl-3-methoxy-6-phenyl-imidazo[1,2-a]pyrazine

HRID 1618097Notes

Reaction equation

HRID 1618097 reaction equation
[CH2:1]([C:8]1[C:29](=[O:30])[N:11]2[CH:12]=[C:13]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[NH:14][C:15]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:10]2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:31](N(C(C)C)CC)(C)C.CI>CN(C=O)C.ClCCl>[CH2:1]([C:8]1[N:9]=[C:10]2[C:15]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:14][C:13]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:12][N:11]2[C:29]=1[O:30][CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 178515551HCID 178515551, compound

Product 1

HCID 667027352,8-Dibenzyl-3-methoxy-6-phenyl-imidazo[1,2-a]pyrazineYield 82.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,8-dibenzyl-6-phenyl-7H-imidazo[1,2-a]pyrazin-3-one (0.25 g, 0.6 mmol) in dry DMF (10 mL) at ambient temperature under argon was added diisopropylethylamine (1.1 mL, 6.0 mmol) all at once, followed by dropwise addition of methyl iodide (0.4 mL, 6.0 mmol). After stirring for 1 h the reaction was complete by TLC analysis. The reaction mixture was diluted with dichloromethane (75 mL) and washed twice with water. The organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated to provide a brown oil. The crude oil was purified by flash chromatography on silica gel (30 g) using dichloromethane as mobile phase. Appropriate fractions were pooled and evaporated to afford 200 mg (77%) of the desired compound.

Workup

  1. washwashed twice with water
  2. dry with materialThe organic extracts were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto provide a brown oil
  6. customThe crude oil was purified by flash chromatography on silica gel (30 g)
  7. customevaporated

Sources & evidence

ORD record
ord-a038531a1d184646b681cf1d79c40b80
Source dataset
uspto-grants-2014_07
Patent number
US08765969B2

Reaction notes

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