Sodium hydride → 4-(2-Nitro-5-(piperidin-1-yl)phenyl)-6-((3-(trifluoromethyl)benzyl)-oxy)pyrimidine

HRID 1407969Notes

Reaction equation

HRID 1407969 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][OH:7].[H-].[Na+].Cl[C:16]1[CH:21]=[C:20]([C:22]2[CH:27]=[C:26]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:25]=[CH:24][C:23]=2[N+:34]([O-:36])=[O:35])[N:19]=[CH:18][N:17]=1>CN(C=O)C>[N+:34]([C:23]1[CH:24]=[CH:25][C:26]([N:28]2[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)=[CH:27][C:22]=1[C:20]1[CH:21]=[C:16]([O:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:4]=2)[N:17]=[CH:18][N:19]=1)([O-:36])=[O:35]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 676813-(Trifluoromethyl)benzylic alcoholHCID 867059284-Chloro-6-(2-nitro-5-(piperidin-1-yl)phenyl)pyrimidine

Product 1

HCID 665880984-(2-Nitro-5-(piperidin-1-yl)phenyl)-6-((3-(trifluoromethyl)benzyl)-oxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 99 mg of 3-(trifluoromethyl)benzyl alcohol in 2 mL of DMF was added 27 mg of a 50% dispersion of sodium hydride in oil. After 15 min the solution was treated with 150 mg of intermediate 3.1b. After an additional 2 h the reaction mixture was partitioned between water and ethyl acetate. The organic extracts were washed with brine and dried (Na2SO4). The solvent was evaporated to give a yellow syrup that was used directly in the next step.

Workup

  1. customAfter an additional 2 h the reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was evaporated
  5. customto give a yellow syrup that

Sources & evidence

ORD record
ord-be59c71033a84efbb44eba9408b2fd45
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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