Methyl iodide → HCID 19742890, compound

HRID 2254894Notes

Reaction equation

HRID 2254894 reaction equation
[Cl:1][C:2]1[C:3]([CH2:48][CH3:49])=[N:4][C:5]([CH2:46][CH3:47])=[CH:6][C:7]=1[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]2[N:23]=[N:24][N:25]([C:27]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:26]=2)=[CH:12][CH:11]=1.[CH3:50]C(C)([O-])C.[K+].O1CCOCCOCCOCCOCCOCC1.IC>C1COCC1>[Cl:1][C:2]1[C:3]([CH2:48][CH3:49])=[N:4][C:5]([CH2:46][CH3:47])=[CH:6][C:7]=1[N:8]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]2[N:23]=[N:24][N:25]([C:27]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:26]=2)=[CH:14][CH:15]=1)[CH3:50]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 2855718-Crown-6HCID 19742898HCID 19742898, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19742890HCID 19742890, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Chloro-2,6-diethyl-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methylamino]pyridine (335 mg) was added to a mixture of potassium t-butoxide (75 mg) and 1,4,7,10,13,16-hexaoxacyclooctadecane (10 mg) in THF (10 ml) and the mixture was stirred for 15 minutes. Iodomethane (0.04 ml) was added and the solution heated at reflux for 6 hours. The mixture was cooled to ambient temperature and solvent was removed by evaporation. The residue was purified by flash chromatography eluting with ethyl acetate/hexane (1:1 v/v) to give 3-chloro-2,6-diethyl-4-[N-(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl-N-methylamino]-pyridine (A) (220 mg) as a foam; NMR (CDCl3): 1.28(double t, 6H), 2.60(s, 3H), 2.72(q, 2H), 2.96(q, 2H), 4.24(s, 2H), 6.59(s, 1H), 6.89(m, 6H), 7.13(m, 3H), 7.30(complex m, 14H), 7.95(m, 1H).

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 6 hours
  3. customsolvent was removed by evaporation
  4. customThe residue was purified by flash chromatography
  5. washeluting with ethyl acetate/hexane (1:1 v/v)

Sources & evidence

ORD record
ord-98227433dfa549108cb833149702e283
Source dataset
uspto-grants-1993_08
Patent number
US05236937

Reaction notes

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