Hydrochloric Acid → 1-((6-Methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde

HRID 1091686ノート

反応式

HRID 1091686 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]1[C:7]([CH:8]=[O:9])=[CH:6][NH:5][N:4]=1.Cl[CH2:13][C:14]1[NH:15][C:16](=[O:24])[C:17]2[CH:22]=[C:21]([CH3:23])[S:20][C:18]=2[N:19]=1.CC(C)([O-])C.[K+].Cl>C1COCC1.CCOC(C)=O.O.CN(C=O)C>[CH3:23][C:21]1[S:20][C:18]2[N:19]=[C:14]([CH2:13][N:5]3[CH:6]=[C:7]([CH:8]=[O:9])[C:3]([C:2]([F:1])([F:10])[F:11])=[N:4]3)[NH:15][C:16](=[O:24])[C:17]=2[CH:22]=1

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 64916832-(Chloromethyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-oneHCID 23665647Potassium tert-butoxideHCID 178519884HCID 178519884、化合物

生成物 1

HCID 866303971-((6-Methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde収率 58.4%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒3 回

実験手順

3-(Trifluoromethyl)-1H-pyrazole-4-carbaldehyde (3.82 g, 23.3 mmol) and 2-(chloromethyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one (5.00 g, 23.3 mmol) were suspended in THF:DMF (180 mL:20 mL) and potassium tert-butoxide (5.23 g, 46.6 mmol) added. The resulting mixture was stirred at RT for 18 h. The mixture was then diluted with EtOAc (500 mL) and shaken with water (200 mL). The separated aqueous phase was acidified to pH 5 with dilute HCl solution and reshaken with the organic layer. The separated organics were then washed with brine (2×200 mL) and dried over MgSO4 before concentration in vacuo. Purification by flash column chromatography-silica gel and elution with 50% isohexane:EtOAc, then EtOAc, gave the desired product as a pale yellow solid (4.65 g, 13.6 mmol, 58%).

後処理

  1. washThe separated organics were then washed with brine (2×200 mL)
  2. dry with materialdried over MgSO4 before concentration in vacuo
  3. customPurification
  4. washby flash column chromatography-silica gel and elution with 50% isohexane

出典と根拠

ORDレコード
ord-383d8b75bd524d6aa21db07431ec43db
出典データセット
uspto-grants-2012_03
特許番号
US08129397B2

反応ノート

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