Sodium hydride → HCID 86676372, compound

HRID 920310Notes

Reaction equation

HRID 920310 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:9]=[C:8]([Cl:10])[CH:7]=[C:6](Cl)[N:5]=1.[OH:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)=[C:18]([CH:21]=1)[C:19]#[N:20]>CN(C)C=O>[Cl:3][C:4]1[N:5]=[C:6]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[CH:24]=3)=[C:18]([CH:21]=2)[C:19]#[N:20])[CH:7]=[C:8]([Cl:10])[N:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 773782,4,6-TrichloropyrimidineHCID 668254365-(Hydroxymethyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrile

Product 1

HCID 86676372HCID 86676372, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (0.532 g, 13.30 mmol) in N, N-dimethylformamide (6 ml) was added 2,4,6-trichloropyrimidine (1.057 g, 5.76 mmol) at 0° C. The reaction mixture was stirred for 5 min at room temperature, and then dropwise was added to a solution of 5-(hydroxymethyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrile (1.3 g, 4.43 mmol) in N, N-dimethylformamide (6 ml). The reaction mixture was stirred for another 1 h at room temperature. Then, the reaction mixture was quenched with water and the solution was purified with reverse phase column chromatography (120 g) using water/MeCN as eluent to afford 5-(((2,6-dichloropyrimidin-4-yl)oxy)methyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrile (1.4 g, 3.18 mmol, 71.7% yield).

Workup

  1. stirringThe reaction mixture was stirred for another 1 h at room temperature
  2. customThen, the reaction mixture was quenched with water
  3. customthe solution was purified with reverse phase column chromatography (120 g)

Sources & evidence

ORD record
ord-6f0c9ded2e8f4c498e7aa2b17d51ba95
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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