Hydrochloric Acid → 7'-bromo-6'-(1H-pyrazol-4-yl)-1'H-spiro [cyclohexane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one

HRID 2364031ノート

反応式

HRID 2364031 の反応式
[Br:1][C:2]1[C:6]2[NH:7][C:8]([CH3:13])([CH3:12])[NH:9][C:10](=[O:11])[C:5]=2[S:4][C:3]=1[C:14]1[CH:15]=[N:16][NH:17][CH:18]=1.Cl.C([O-])(O)=O.[Na+].[O-]S([O-])(=O)=O.[Mg+2].[C:31]1(=O)[CH2:36]CCC[CH2:32]1.CC1C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C.CO>[Br:1][C:2]1[C:6]2[NH:7][C:8]3([CH2:12][CH2:36][CH2:31][CH2:32][CH2:13]3)[NH:9][C:10](=[O:11])[C:5]=2[S:4][C:3]=1[C:14]1[CH:15]=[N:16][NH:17][CH:18]=1

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 667432407-bromo-2,2-dimethyl-6-(1H-pyrazol-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

生成物 1

HCID 667432907'-bromo-6'-(1H-pyrazol-4-yl)-1'H-spiro [cyclohexane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one収率 30.1%

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 7-bromo-2,2-dimethyl-6-(1H-pyrazol-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (50 mg, 0.153 mmol), 1 M HCl (0.5 mL, 0.50 mmol) and MeOH (2.5 mL) was stirred at 50° C. After 1 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 mixed with MgSO4 (18.4 mg, 0.153 mmol), cyclohexanone (1 mL, 9.65 mmol), PTSA (2.9 mg, 0.015 mmol) and DMF (1 mL). The mixture was stirred at 80° C. for 1 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, hexane to EtOAc). Then, the obtained oil was triturated with EtOAc, and the precipitate was collected by filtration to afford the title compound (16.9 mg, 30%) as a pale 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 1 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, hexane to EtOAc)
  11. customThen, the obtained oil was triturated with EtOAc
  12. filtrationthe precipitate was collected by filtration

出典と根拠

ORDレコード
ord-2d89bc6468a04debbec6aebef12bc3c9
出典データセット
uspto-grants-2014_04
特許番号
US08691828B2

反応ノート

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