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 7651

反応式

HRID 7651 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-08396a805534465c9d2391dc3eb2f269
出典データセット
uspto-grants-2006_08
特許番号
US07087615B2

関連ノート

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