Tetrahydrofuran → HCID 21708383, compound

HRID 651424Notes

Reaction equation

HRID 651424 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.C1COCC1.Cl.[CH3:40][NH:41][CH3:42].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:40][N:41]([CH3:42])[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:20])[F:21])[CH:14]=2)[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]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 21708393HCID 21708393, compound

Product 1

HCID 21708383HCID 21708383, compoundYield 110.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(Ethylsulfonyl)-4-[m-(trifluoromethyl)benzyl]-6-[(α,α,α-trifluoro-m-tolyl)oxy]pyrimidine (0.40 g, 0.82 mmol) is added to THF (20 ml). Dimethylamine hydrochloride (0.11 g, 13.4 mmol) and triethylamine (0.17 g, 16.8 mmol) is added and the reaction stirred at room temperature for 18 days. Ethyl acetate is added to the reaction and the organic phase is washed with water, brine and dried over magnesium sulfate. The solvent is removed under vacuum and the residue is chromatographed to afford 0.40 g 2-(Dimethylamino)-4-[m-(trifluoromethyl)-benzyl]-6-[(α,α,α-trifluoro-m-tolyl)oxy]pyrimidine as a yellow oil. 1H NMR CDCl3 3.02 (6H, b) 3.92 (2H, s) 5.87 (1H, s) 7.3-7.65 (8H, m).

Workup

  1. washthe organic phase is washed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent is removed under vacuum
  4. customthe residue is chromatographed

Sources & evidence

ORD record
ord-43c2beadc5b84201b5b530b91088ac10
Source dataset
uspto-grants-2001_08
Patent number
US06281219B1

Reaction notes

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