Dihydrouracil → 1-{4-[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]butyl}dihydropyrimidine-2,4(1H,3H)-dione

HRID 1245341Notes

Reaction equation

HRID 1245341 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:22]=[CH:21][C:13]2[C:14]([C:17]([F:20])([F:19])[F:18])=[N:15][O:16][C:12]=2[C:11]=1[CH2:23][CH2:24][CH3:25])(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+].[NH:32]1[CH2:39][CH2:38][C:36](=[O:37])[NH:35][C:33]1=[O:34]>CN(C=O)C>[CH2:23]([C:11]1[C:12]2[O:16][N:15]=[C:14]([C:17]([F:20])([F:19])[F:18])[C:13]=2[CH:21]=[CH:22][C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6][N:32]1[CH2:39][CH2:38][C:36](=[O:37])[NH:35][C:33]1=[O:34])[CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 649DihydrouracilHCID 10796Cesium carbonateHCID 219109934-[7-Propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]butyl methanesulfonate

Product 1

HCID 219110301-{4-[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]butyl}dihydropyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]butyl methanesulfonate (60 mg, 0.16 mmol), from this Example step 5, Cs2CO3 (206 mg, 0.63 mmol) and 5,6-dihydrouracil (54.2 mg, 0.48 mmol) in dry DMF (1.5 mL) was stirred at room temperature overnight. The reaction mixture was 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 residue was purified by preparative TLC using ethyl acetate to give the title compound.

Workup

  1. customwas stirred at room temperature overnight
  2. customThe reaction mixture was partitioned 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 residue was purified by preparative TLC

Sources & evidence

ORD record
ord-7ddbc9cd13e045ecbe211289e43f59e9
Source dataset
uspto-grants-2006_10
Patent number
US07125865B2

Reaction notes

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