Water → HCID 54322478, compound

HRID 266067Notes

Reaction equation

HRID 266067 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[N:20]=[CH:19][C:18]([N:21]4[CH:25]=[N:24][NH:23][C:22]4=[O:26])=[CH:17][N:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH:38]([CH2:48][CH3:49])[C:39]([C:41]1[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=1)=[O:40].O>O1CCCC1.CN(C)C=O>[Cl:47][C:44]1[CH:43]=[CH:42][C:41]([C:39]([CH:38]([N:23]2[C:22](=[O:26])[N:21]([C:18]3[CH:17]=[N:16][C:15]([N:12]4[CH2:11][CH2:10][N:9]([C:6]5[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=5)[CH2:14][CH2:13]4)=[N:20][CH:19]=3)[CH:25]=[N:24]2)[CH2:48][CH3:49])=[O:40])=[CH:46][CH:45]=1

Participants

7

Reactant 4

HCID 962WaterHCID 2724254Sodium bis(trimethylsilyl)amideHCID 15896015HCID 15896015, compoundHCID 19032412HCID 19032412, compound

Product 1

HCID 54322478HCID 54322478, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2,4-Dihydro-4-[2-[4-(4-methoxyphenyl)-1-piperazinyl]-5-pyrimidinyl]-3H-1,2,4-triazol-3-one (0.019 mol) and N,N-dimethylformamide (200 ml) were stirred. A solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (1M) (21 ml) was added dropwise under N2 and the mixture was stirred for 30 minutes at room temperature. 2-Bromo-1-(4-chlorophenyl)-1-butanone (0.021 mol) dissolved in a little N,N-dimethylformamide was added dropwise and the mixture was stirred for 3 hours at room temperature. The mixture was poured into water and extracted with dichloromethane. The organic layer was washed with water, dried and evaporated. The residue was crystallized from 1-propanol. The precipitate was faltered off and dried in vacuo at 75° C., yielding 6 g (60%) of (±)-2-[1 -(4-chlorobenzoyl)propyl]-2,4-dihydro-4-[2-[4-(4-methoxyphenyl)-1-piperazinyl]-5-pyrimidinyl]-3H-1,2,4-triazol-3-one; mp. 184.6° C. (comp. 8).

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred for 3 hours at room temperature
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with water
  5. customdried
  6. customevaporated
  7. customThe residue was crystallized from 1-propanol
  8. customdried in vacuo at 75° C.

Sources & evidence

ORD record
ord-cc20b5e0df914e28bf16baffd41d0436
Source dataset
uspto-grants-1997_07
Patent number
US05650411

Reaction notes

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