Sodium hydride → HCID 178491462, compound

HRID 1786306Notes

Reaction equation

HRID 1786306 reaction equation
[CH:1]1([C:8]2[N:13]3[N:14]=[CH:15][N:16]=[C:12]3[N:11]=[C:10]([OH:17])[C:9]=2[C:18]2[C:23]([F:24])=[CH:22][C:21](F)=[CH:20][C:19]=2[F:26])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:27][O:28][C:29]1[CH:40]=[CH:39][C:32]([CH2:33][O:34][CH2:35][CH2:36][CH2:37][OH:38])=[CH:31][CH:30]=1.[H-].[Na+]>CS(C)=O>[CH:1]1([C:8]2[N:13]3[N:14]=[CH:15][N:16]=[C:12]3[N:11]=[C:10]([OH:17])[C:9]=2[C:18]2[C:23]([F:24])=[CH:22][C:21]([O:38][CH2:37][CH2:36][CH2:35][O:34][CH2:33][C:32]3[CH:31]=[CH:30][C:29]([O:28][CH3:27])=[CH:40][CH:39]=3)=[CH:20][C:19]=2[F:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 109764011-Propanol, 3-[(4-methoxyphenyl)methoxy]-HCID 178517386HCID 178517386, compound

Product 1

HCID 178491462HCID 178491462, compoundYield 152.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 7-cycloheptyl-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-5-ol (362 mg, 1.0 mmol) and 3-[(4-methoxybenzyl)oxy]-1-propanol (490 mg, 2.5 mmol) in 4.0 mL of dimethylsulfoxide at room temperature is added sodium hydride (60% in mineral oil, 120 mg, 3.0 mmol). The mixture is stirred at room temperature for 3 h, and partitioned between ethyl acetate and 1.0 N hydrochloric acid. The organic solution is washed with saturated sodium chloride, dried over magnesium sulfate, and concentrated to a residue. The residue is chromatographed over silica gel, eluting with a gradient of 66% ethyl acetate in hexanes to 5% methyl alcohol in ethyl acetate. Concentration provides 7-cycloheptyl-6-(2,6-difluoro-4-{3-[(4-methoxybenzyl)oxy]propoxy}phenyl)[1,2,4]triazolo[1,5-a]pyrimidin-5-ol as a yellow oil (820 mg).

Workup

  1. custompartitioned between ethyl acetate and 1.0 N hydrochloric acid
  2. washThe organic solution is washed with saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to a residue
  5. customThe residue is chromatographed over silica gel
  6. washeluting with a gradient of 66% ethyl acetate in hexanes to 5% methyl alcohol in ethyl acetate
  7. concentrationConcentration

Sources & evidence

ORD record
ord-12ea2415dfc34ab38ffedece9c45e59f
Source dataset
uspto-grants-2009_03
Patent number
US07507739B2

Reaction notes

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