Sodium hydride → 2-(4-fluorophenyl)-6-methoxy-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

HRID 1061635

반응식

HRID 1061635 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]2[CH2:15][CH:14]([O:16][CH3:17])[CH2:13][N:12]2[C:18]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([S:26][CH3:27])[N:21]=2)=O)=[O:10])=[CH:4][CH:3]=1.CN(C)C=O.O1CCCC1.[H-].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:10])[N:11]3[CH2:15][CH:14]([O:16][CH3:17])[CH2:13][N:12]3[C:18]=2[C:20]2[CH:25]=[CH:24][N:23]=[C:22]([S:26][CH3:27])[N:21]=2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 21974620tetrahydrofuran N,N-dimethylformamideHCID 219921822-(4-Fluorophenyl)-1-[4-methoxy-2-(2-methylsulfanyl-pyrimidine-4-carbonyl)pyrazolidine-1-yl]-ethanone

생성물 1

HCID 219921842-(4-fluorophenyl)-6-methoxy-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one수율 57%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 2-(4-fluorophenyl)-1-[4-methoxy-2-(2-methylsulfanyl-pyrimidine-4-carbonyl)pyrazolidine-1-yl]-ethanone, 48, (2.04 g, 5.22 mmol) in 1:1 dimethylformamide/tetrahydrofuran (30 mL) is added dropwise to a 0° C. suspension of sodium hydride (230 mg of a 60% dispersion in mineral oil, 5.75 mmol) in dimethylformamide (60 mL). After 2 hours at 0° C., the bright red solution is quenched by slow addition of a saturated aqueous solution of ammonium chloride (5 mL). The cold bath is removed, and the solution allowed to warm to room temperature. The reaction mixture is concentrated in vacuo and the resultant residue diluted with ethyl acetate (175 mL). The mixture is washed with a saturated aqueous solution of ammonium chloride (150 mL). The aqueous layer is extracted with ethyl acetate (4×75 mL). The combined organic layers are dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material is purified over silica gel (100% ethyl acetate to 5% to 10% to 20% methyl alcohol/ethyl acetate) to afford 1.1 g (57% yield) of the desired product as an orange oil.

후처리

  1. customthe bright red solution is quenched by slow addition of a saturated aqueous solution of ammonium chloride (5 mL)
  2. customThe cold bath is removed
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. additionthe resultant residue diluted with ethyl acetate (175 mL)
  5. washThe mixture is washed with a saturated aqueous solution of ammonium chloride (150 mL)
  6. extractionThe aqueous layer is extracted with ethyl acetate (4×75 mL)
  7. dry with materialThe combined organic layers are dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude material is purified over silica gel (100% ethyl acetate to 5% to 10% to 20% methyl alcohol/ethyl acetate)

출처 및 근거

ORD 기록
ord-2f9463eca2f3454dbceb8939b591cc30
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960593B2

연결된 노트

불러오는 중…