Cesium carbonate → 5-phenyl-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)dihydropyrimidine-2,4(1H,3H)-dione

HRID 1245342Notes

Reaction equation

HRID 1245342 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:18]=[CH:17][C:9]2[C:10]([C:13]([F:16])([F:15])[F:14])=[N:11][O:12][C:8]=2[C:7]=1[CH2:19][CH2:20][CH3:21].BrC(Cl)CC.[C:27]1([CH:33]2[CH2:38][NH:37][C:36](=[O:39])[NH:35][C:34]2=[O:40])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[C:27]1([CH:33]2[CH2:38][NH:37][C:36](=[O:39])[N:35]([CH2:2][CH2:3][CH2:4][O:5][C:6]3[CH:18]=[CH:17][C:9]4[C:10]([C:13]([F:16])([F:15])[F:14])=[N:11][O:12][C:8]=4[C:7]=3[CH2:19][CH2:20][CH3:21])[C:34]2=[O:40])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 36872Propane, bromochloro-HCID 219110296-(3-Chloropropoxy)-7-propyl-3-(trifluoromethyl)-1,2-benzisoxazoleHCID 587195655-phenyldihydropyrimidine-2,4(1H,3H)-dione

Product 1

HCID 219110165-phenyl-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)dihydropyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-(3-chloropropoxy)-7-propyl-3-(trifluoromethyl)-1,2-benzisoxazole, prepared as for Example 7 from bromochloropropane, (36 mg, 0.12 mmol), 5-phenyldihydropyrimidine-2,4(1H,3H)-dione, from this Example step 1, (42.5 mg, 0.22 mmol), Cs2CO3 (145.7 mg, 0.45 mmol) and KI (9.3 mg, 0.056 mmol) in dry DMF was stirred at room temperature overnight. The reaction mixture was diluted with water and partitioned between ethyl acetate and water. Combined organic extracts were washed with water and brine, dried over Na2SO4 and the solvent evaporated in vacuo. The product was purified by HPLC using 30% to 70% gradient CH3CN:H2O).

Workup

  1. customwas stirred at room temperature overnight
  2. custompartitioned between ethyl acetate and water
  3. washCombined organic extracts were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent evaporated in vacuo
  6. customThe product was purified by HPLC

Sources & evidence

ORD record
ord-40347162d24d420facdf46fbc02da755
Source dataset
uspto-grants-2006_10
Patent number
US07125865B2

Reaction notes

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