5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1, 2-benzisothiazole-3-carboxaldehyde → HCID 22119976, compound

HRID 1274635Notes

Reaction equation

HRID 1274635 reaction equation
[CH3:1][Mg]Cl.[CH3:4][N:5]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:8](=[O:15])[N:7]([C:16]2[CH:17]=[CH:18][C:19]3[S:23][N:22]=[C:21]([CH:24]=[O:25])[C:20]=3[CH:26]=2)[C:6]1=[O:27]>O1CCCC1>[OH:25][CH:24]([C:21]1[C:20]2[CH:26]=[C:16]([N:7]3[C:8](=[O:15])[CH:9]=[C:10]([C:11]([F:12])([F:13])[F:14])[N:5]([CH3:4])[C:6]3=[O:27])[CH:17]=[CH:18][C:19]=2[S:23][N:22]=1)[CH3:1]

Participants

4

Reactant 2

HCID 178523685-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1, 2-benzisothiazole-3-carboxaldehydeHCID 178418332HCID 178418332, compound

Product 1

HCID 22119976HCID 22119976, compoundYield 711.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl magnesium chloride (14.1 ml, 0.0422 mol) is added dropwise to a solution of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxaldehyde (6.00 g, 0.00170 mol) in tetrahydrofuran at -78° C. over 15 minutes. The resultant mixture is stirred at -78° C. for 30 minutes, quenched with saturated ammonium chloride and allowed to warm to room temperature. After dilution with ethyl acetate, the mixture is washed with saturated ammonium chloride, water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to a solid. The solid is chromatographed on silica gel with hexanes/ethyl acetate to give the title compound as a white crystalline solid (4.49 g, 71.1%) which is identified by NMR spectral analysis.

Workup

  1. customquenched with saturated ammonium chloride
  2. washAfter dilution with ethyl acetate, the mixture is washed with saturated ammonium chloride, water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a solid
  6. customThe solid is chromatographed on silica gel with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-14278dd882e844fbaa8d590d632a92b6
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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