Methyl iodide → HCID 136105554, compound

HRID 2244109Notes

Reaction equation

HRID 2244109 reaction equation
[H-].[Na+].C[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:20]=[C:19]([NH:21][CH2:22][C:23]2[O:24][C:25]([CH3:28])=[N:26][N:27]=2)[C:18]2[C:13](=[CH:14][C:15]([CH3:29])=[CH:16][CH:17]=2)[N:12]=1.[CH3:30]I>CN(C=O)C>[CH3:29][C:15]1[CH:14]=[C:13]2[C:18]([C:19]([N:21]([CH3:30])[CH2:22][C:23]3[O:24][C:25]([CH3:28])=[N:26][N:27]=3)=[N:20][C:11]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[OH:4])=[N:12]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59212929HCID 59212929, compound

Product 1

HCID 136105554HCID 136105554, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[2-(2-Methoxy-phenyl)-7-methyl-quinazolin-4-yl]-methyl-(5-methyl-[1,3,4]oxadiazol-2-ylmethyl)-anine To a stirring suspension of freshly washed sodium hydride (42 mg, 1.04 mmol) in dry DMF at 0° C. under a nitrogen atmosphere was added the [2-(2-Methoxy-phenyl)-7-methyl-quinazolin-4-yl]-(5-methyl-[1,3,4]oxadiazol-2-ylmethyl)-amine (180 mg, 0.518 mmol, in 5 ml DMF). After 30 minutes at 0° C., MeI (74 μl, 1.19 mmol) was added and the reaction was allowed to warm to room temperature. After one hour the reaction was quenched with water and extracted 3 times with EtOAc. Organics were combined, dried over MgSO4, filtered and concentrated to a yellow oil. Purified by flash chromatography 50/50 EtOAc/hexanes to afford the desired product as a clear oil. 128 mg, 66% yield. LC/MS (10-99%) M/Z 376.1, retention time 2.06 minutes.

Workup

  1. customAfter one hour the reaction was quenched with water
  2. extractionextracted 3 times with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a yellow oil
  6. customPurified by flash chromatography 50/50 EtOAc/hexanes

Sources & evidence

ORD record
ord-4e37e5d22ff741d9977a2a6e00b6c6d7
Source dataset
uspto-grants-2010_03
Patent number
US07678802B2

Reaction notes

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