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Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 7-bromo-2-methyl-6-(1H-pyrazol-4-yl)-2-(2,2,2-trifluoroethyl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

HRID 2364048
ノート
印刷プレビュー

反応式

HRID 2364048 の反応式
[NH2:1][C:2]1[C:6]([Br:7])=[C:5]([C:8]2[CH:9]=[N:10][NH:11][CH:12]=2)[S:4][C:3]=1[C:13]([NH2:15])=[O:14].[F:16][C:17]([F:23])([F:22])[CH2:18][C:19](=O)[CH3:20].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[O-]S([O-])(=O)=O.[Mg+2].C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[Br:7][C:6]1[C:2]2[NH:1][C:19]([CH3:20])([CH2:18][C:17]([F:23])([F:22])[F:16])[NH:15][C:13](=[O:14])[C:3]=2[S:4][C:5]=1[C:8]1[CH:9]=[N:10][NH:11][CH:12]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 5390014,4,4-Trifluorobutan-2-oneHCID 667431873-amino-4-bromo-5-(1H-pyrazol-4-yl)thiophene-2-carboxamide

生成物 1

HCID 66744070
7-bromo-2-methyl-6-(1H-pyrazol-4-yl)-2-(2,2,2-trifluoroethyl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one
収率 24%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

A mixture of 3-amino-4-bromo-5-(1H-pyrazol-4-yl)thiophene-2-carboxamide (90 mg, 0.313 mmol), 4,4,4-trifluorobutan-2-one (395 mg, 3.13 mmol), CSA (7.28 mg, 0.031 mmol), MgSO4 (37.7 mg, 0.313 mmol) and DMA (2 mL) was microwave-irradiated at 150° 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). The obtained solid was triturated with EtOAc, and the precipitate was collected by filtration to afford the title compound (29.2 mg, 24%) as a white solid:

後処理

  1. customwas microwave-irradiated at 150° C. for 3 h
  2. extractionextracted with EtOAc
  3. dry with materialthe extract was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc)
  7. customThe obtained solid was triturated with EtOAc
  8. filtrationthe precipitate was collected by filtration

出典と根拠

ORDレコード
ord-059b5d5a60784be2a8789d71554fd99a
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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