Methyl iodide → HCID 23121934, compound

HRID 1713519Notes

Reaction equation

HRID 1713519 reaction equation
[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:12])[CH2:10][CH:5]2[C:4]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:3]1.[H-].[Na+].[CH3:34]I>O1CCCC1>[CH3:34][N:13]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:11]([N:9]1[CH2:8][CH2:7][N:6]2[C:2](=[O:1])[O:3][C:4]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:5]2[CH2:10]1)=[O:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23121998HCID 23121998, compound

Product 1

HCID 23121934HCID 23121934, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tetrahydro-3-oxo-N,1,1-triphenyl-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxamide (60 mg, 0.15 mmol) in tetrahydrofuran (2 mL) was added 60% sodium hydride (10 mg, 0.25 mmol), and the mixture was stirred at room temperature for 1 hour. Next, methyl iodide (0.15 g, 1.1 mmol) was added thereto, and the mixture was stirred at room temperature for 4 hours. The reaction solution was concentrated. Then, the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1) and crystallized from diisopropyl ether to obtain the title compound (30 mg, yield 48%).

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. concentrationThe reaction solution was concentrated
  3. customThen, the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1)
  4. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-61cd45d049ad4394a9ac717f79c5875c
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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