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

HRID 1061617

반응식

HRID 1061617 반응식
[CH3:1][N:2]([CH3:28])[CH:3]1[CH2:7][N:6]([C:8](=[O:17])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:5]([C:18]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([S:26][CH3:27])[N:21]=2)=O)[CH2:4]1.[H-].[Na+]>C1COCC1>[CH3:1][N:2]([CH3:28])[CH:3]1[CH2:7][N:6]2[C:8](=[O:17])[C:9]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:18]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([S:26][CH3:27])[N:21]=3)[N:5]2[CH2:4]1

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 219922051-[4-Dimethylamino-2-(2-methylsulfanyl-pyrimidine-4-carbonyl) pyrazolidin-1-yl]-2-(4-fluorophenyl)-ethanone

생성물 1

HCID 219922076-dimethylamino-2-(4-fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

1-[4-Dimethylamino-2-(2-methylsulfanyl-pyrimidine-4-carbonyl)-pyrazolidin-1-yl]-2-(4-fluorophenyl)-ethanone, 23, (4.0 g, 10 mmol) is dissolved in THF (75 mL). This solution is then added dropwise via cannula to a suspension of NaH (0.440 g of a 60% dispersion in mineral oil, 11 mmol) at −30° C. The reaction is allowed to gradually warm to 0° C. over 3 hours. The reaction is quenched with NH4Cl (sat. aq.) (15 mL). The mixture is stirred at room temperature, then concentrated in vacuo. The residue is diluted with tetrahydrofuran (250 mL) and the mixture filtered through Celite. The filtrate is concentrated in vacuo to give an oil. The crude product is purified over silica (100% ethyl acetate to 5% to 10% to 20% methyl alcohol/ethyl acetate) to afford the desired product.

후처리

  1. customThe reaction is quenched with NH4Cl (sat. aq.) (15 mL)
  2. concentrationconcentrated in vacuo
  3. additionThe residue is diluted with tetrahydrofuran (250 mL)
  4. filtrationthe mixture filtered through Celite
  5. concentrationThe filtrate is concentrated in vacuo
  6. customto give an oil
  7. customThe crude product is purified over silica (100% ethyl acetate to 5% to 10% to 20% methyl alcohol/ethyl acetate)

출처 및 근거

ORD 기록
ord-05475286578e4151a9dcf3cf6384c4e8
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960593B2

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