Ethanol → HCID 21708397, compound

HRID 651423Notes

Reaction equation

HRID 651423 reaction equation
C(S([C:6]1[N:11]=[C:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[CH:9]=[C:8]([O:23][C:24]2[CH:25]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:28][CH:29]=2)[N:7]=1)(=O)=O)C.C(Cl)(Cl)Cl.C(O)C.[BH4-].[Na+]>C(OCC)(=O)C>[F:22][C:19]([F:20])([F:21])[C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][C:10]1[CH:9]=[C:8]([O:23][C:24]2[CH:25]=[C:26]([C:30]([F:31])([F:32])[F:33])[CH:27]=[CH:28][CH:29]=2)[N:7]=[CH:6][N:11]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 21708393HCID 21708393, compound

Product 1

HCID 21708397HCID 21708397, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(Ethylsulfonyl)-4-[m-(trifluoromethyl)benzyl] -6-[(α,α,α-trifluoro-m-tolyl)oxy]pyrimidine (1.17 g, 2.4 mmol) is added to chloroform (10 ml) and ethanol (10 ml). sodium borohydride (0.3 g, 7.9 mmol) is added portionwise over 15 minutes and the reaction is stirred at room temperature for 80 mins. The mixture is taken up in ethyl acetate and is washed with water, brine and dried over magnesium sulfate. The solvent is evaporated to give 1.05 g of a cloudy oil which is chromatographed to yield 0.89 g 4-[m-(trifluoromethyl)benzyl]-6-[(α,α,α-trifluoro-m-tolyl)oxy]pyrimidine as a water white oil. 1H NMR CDCl3 4.17 (2H, s) 6.75 (1H,s) 7.3-7.6 (8H, m) 8.71 (1H, s)

Workup

  1. washis washed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent is evaporated
  4. customto give 1.05 g of a cloudy oil which
  5. customis chromatographed

Sources & evidence

ORD record
ord-a90ffa137fd34dc59635f384c2698a7e
Source dataset
uspto-grants-2001_08
Patent number
US06281219B1

Reaction notes

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