Acetone → 7-bromo-2,2-dimethyl-6-(1H-pyrazol-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

HRID 2364030ノート

反応式

HRID 2364030 の反応式
[CH3:1][C:2]1([CH3:17])[NH:7][C:6]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][NH:14][CH:15]=3)[S:10][C:5]=2[C:4](=[O:16])[NH:3]1.[Br:18]Br.C([O-])(O)=O.[Na+].CC(C)=O.CC1C=CC(S(O)(=O)=O)=CC=1.[O-]S([O-])(=O)=O.[Mg+2]>C(O)(=O)C.CN(C=O)C>[Br:18][C:8]1[C:6]2[NH:7][C:2]([CH3:17])([CH3:1])[NH:3][C:4](=[O:16])[C:5]=2[S:10][C:9]=1[C:11]1[CH:15]=[N:14][NH:13][CH:12]=1

参加物

9

反応物 6

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 24408BromineHCID 516892Sodium Bicarbonate2 回HCID 667438422,2-dimethyl-6-(1H-pyrazol-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

生成物 1

HCID 667432407-bromo-2,2-dimethyl-6-(1H-pyrazol-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one収率 30.6%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 2,2-dimethyl-6-(1H-pyrazol-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (248 mg, 1.00 mmol) in acetic acid (5 mL) was added slowly bromine (0.077 mL, 1.50 mmol) with vigorous stirring. After 3 min, 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 to give a yellow solid. This residue was mixed with acetone (5.0 mL, 68.1 mmol), PTSA (9.5 mg, 0.050 mmol), MgSO4 (120 mg, 1.00 mmol) and DMF (1 mL). This mixture was stirred at 60° C. for 1 h. Then, 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 (silica gel, hexane to EtOAc) to give a pale yellow solid (100 mg). This solid was triturated with EtOAc and collected by filtration to afford the title compound (69.9 mg, 21%) 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. customto give a yellow solid
  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 (silica gel, hexane to EtOAc)

出典と根拠

ORDレコード
ord-11a19a1bad274f2987b4853765e59626
出典データセット
uspto-grants-2014_04
特許番号
US08691828B2

反応ノート

読み込み中…