Water → HCID 15171324, compound

HRID 1614767Notes

Reaction equation

HRID 1614767 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:9]([CH2:10][OH:11])=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[N:27]=[N:28][N:29]([C:31]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:30]=3)=[CH:16][CH:15]=2)[CH:7]=[C:6]([CH3:50])[N:5]=1.I[CH3:52].O.CN([CH:57]=[O:58])C>>[CH3:3][C:4]1[C:9]([C:10]([O:58][CH2:57][CH3:52])=[O:11])=[C:8]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[N:27]=[N:28][N:29]([C:31]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[N:30]=3)=[CH:18][CH:19]=2)[CH:7]=[C:6]([CH3:50])[N:5]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14950483HCID 14950483, compound

Product 1

HCID 15171324HCID 15171324, compound

Procedure

Sodium hydride (115 mg) was added to a solution of 2,6-dimethyl-3-hydroxymethyl-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]pyridine (1.0 g) in DMF (30 ml) and the mixture was stirred for 10 minutes. Iodomethane (0.3 ml) was added and the mixture was stirred for 18 hours. Water (100 ml) was added and the mixture was extracted with ethyl acetate (2×50 ml). The combined extracts were washed with saturated sodium chloride solution (50 ml) and then dried (MgSO4). The solvent was removed by evaporation and the residue was purified by flash chromatography, eluting with a mixture of methanol and dichloromethane on a gradient from 1:50 v/v to 1:20 v/v, to give 2,6-dimethyl-3-methoxymethyl-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]pyridine (A) (0.74 g), m.p. 132°-135° C.; NMR (d6 -DMSO/d4 -acetic acid): 2.55(s,6H), 3.2(s,3H), 4.45(s,2H), 5.25(s,2H), 6.8-7.9 (complex m,24H).

Workup

  1. stirringthe mixture was stirred for 18 hours
  2. extractionthe mixture was extracted with ethyl acetate (2×50 ml)
  3. washThe combined extracts were washed with saturated sodium chloride solution (50 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed by evaporation
  6. customthe residue was purified by flash chromatography
  7. washeluting with a mixture of methanol and dichloromethane on a gradient from 1:50 v/v to 1:20 v/v

Sources & evidence

ORD record
ord-5eded0bdb5cc4acb9411b13c120b1908
Source dataset
uspto-grants-1993_03
Patent number
US05198439

Reaction notes

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