Methyl iodide → HCID 136105554, compound

HRID 1798766Notes

Reaction equation

HRID 1798766 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:18]=[C:17]([N:19]([CH3:27])[CH2:20][C:21]2[O:22][C:23]([CH3:26])=[N:24][N:25]=2)[C:16]2[C:11](=[CH:12][C:13]([CH3:28])=[CH:14][CH:15]=2)[N:10]=1.[H-].[Na+].COC1C=CC=CC=1C1N=C(NCC2OC(C)=NN=2)C2C(=CC(C)=CC=2)N=1.CI>CN(C=O)C>[CH3:28][C:13]1[CH:12]=[C:11]2[C:16]([C:17]([N:19]([CH3:27])[CH2:20][C:21]3[O:22][C:23]([CH3:26])=[N:24][N:25]=3)=[N:18][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[OH:2])=[N:10]2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59212929HCID 59212929, compoundHCID 59213714HCID 59213714, 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)-amine 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-289d5c7a03ab4d52aced0c893101d7a4
Source dataset
uspto-grants-2013_01
Patent number
US08343980B2

Reaction notes

Loading…