Methyl iodide → HCID 10137537, compound

HRID 2183541Notes

Reaction equation

HRID 2183541 reaction equation
[Br:1][C:2]1[C:3]([NH:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[C:4]2[N:11]=[N:10][N:9]([C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])[C:5]2=[N:6][C:7]=1[CH3:8].[Li][CH2:28]CCC.CI>C1COCC1.CCCCCC>[Br:1][C:2]1[C:3]([N:21]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH3:28])=[C:4]2[N:11]=[N:10][N:9]([C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])[C:5]2=[N:6][C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 22474363HCID 22474363, compoundHCID 178418339Butyllithium

Product 1

HCID 10137537HCID 10137537, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of [6-bromo-5-methyl-3-(2,4,6-trimethyl-phenyl)-3H-[1,2,3]triazolo[4,5-b]pyridin-7-yl]-(1-ethyl-propyl)-amine (50 mg, 0.12 mmol) in dry THF )1.5 ml) was added 2.5 M n-BuLi in hexane (0.14 ml) at −78° C. After stirring at −78° C. for 10 min, 0.5 ml of methyl iodide was added at that temperature then allowed to warmed to room temperature and stirred for 15 min for 2 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give 46 mg of brown oil. The residue was purified through silica gel coliumn chromatography using 1:1 chloroform:hexane as eluent to give the title compound as a golden oil. 1H NMR (CDCl3) ä 7.04(s, 2H), 4.35(m, 1H), 3.32(s, 3H), 2.70(s, 3H), 2.38(s, 3H), 1.94(s, 6H), 1.7-2.0(m, 4H), 1.01(t, 6H)ppm.

Workup

  1. temperatureto warmed to room temperature
  2. stirringstirred for 15 min for 2 hours
  3. customThe mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8b5081ad7b2d4de7bdec3dbf6a32d151
Source dataset
uspto-grants-2005_05
Patent number
US06900217B2

Reaction notes

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