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Hydrochloric Acid → 6'-(5-methyl-1H-pyrazol-4-yl)-1'H-spiro [cyclohexane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one

HRID 2364034
ノート
印刷プレビュー

反応式

HRID 2364034 の反応式
[CH3:1][C:2]1([CH3:18])[NH:7][C:6]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][NH:14][C:15]=3[CH3:16])[S:10][C:5]=2[C:4](=[O:17])[NH:3]1.Cl.C([O-])(O)=O.[Na+].[C:25]1(=O)[CH2:30]CCC[CH2:26]1.[O-]S([O-])(=O)=O.[Mg+2].CC1C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C.CO>[CH3:16][C:15]1[NH:14][N:13]=[CH:12][C:11]=1[C:9]1[S:10][C:5]2[C:4](=[O:17])[NH:3][C:2]3([CH2:18][CH2:30][CH2:25][CH2:26][CH2:1]3)[NH:7][C:6]=2[CH:8]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 7967CyclohexanoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium Bicarbonate2 回HCID 66743505Cdc7-IN-15

生成物 1

HCID 66743431
6'-(5-methyl-1H-pyrazol-4-yl)-1'H-spiro [cyclohexane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one
収率 41.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of 2,2-dimethyl-6-(5-methyl-1H-pyrazol-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (0.090 g, 0.343 mmol), 1 M HCl (1.2 mL, 1.2 mmol) and MeOH (4 mL) was stirred at 50° C. for 2 h. Then, the reaction mixture was poured into excess saturated aqueous NaHCO3 and extracted with EtOAc, and the extract was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was mixed with cyclohexanone (2 mL, 19.3 mmol), MgSO4 (0.041 g, 0.343 mmol), PTSA (3.3 mg, 0.017 mmol) and DMF (2 mL). The mixture was stirred at 80° C. for 3 h. The mixture was poured into saturated aqueous NaHCO3 and extracted with EtOAc, and the extract was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc then to 90:10 EtOAc/MeOH). The obtained oil was purified again by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc) to give a yellow solid. This solid was triturated with EtOAc/hexane and collected by filtration to afford the title compound (42.8 mg, 41%) as a yellow solid:

後処理

  1. extractionextracted with EtOAc
  2. dry with materialthe extract was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. stirringThe mixture was stirred at 80° C. for 3 h
  6. extractionextracted with EtOAc
  7. dry with materialthe extract was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc
  11. customThe obtained oil was purified again by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc)
  12. customto give a yellow solid
  13. customThis solid was triturated with EtOAc/hexane
  14. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-01c7d3d0bdcb466c8799809109955355
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08691828B2

反応ノート

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