Cyclohexanone → 6'-(pyridin-4-yl)-1'H-spiro[cyclohexane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one

HRID 2363930ノート

反応式

HRID 2363930 の反応式
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([NH2:15])=[O:14].[C:16]1(=O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[N:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]3[C:13](=[O:14])[NH:15][C:16]4([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)[NH:1][C:2]=3[CH:6]=2)=[CH:12][CH:11]=1

参加物

6

反応物 4

HCID 7967CyclohexanoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 99208523-Amino-5-(pyridin-4-yl)thiophene-2-carboxamide

生成物 1

HCID 667442146'-(pyridin-4-yl)-1'H-spiro[cyclohexane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one収率 36%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

A mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (0.110 g, 0.500 mmol), cyclohexanone (0.245 g, 2.50 mmol), p-toluenesulfonic acid monohydrate (0.105 g, 0.550 mmol) and toluene (5.0 mL) was stirred for 1 h at 90° C. The mixture was poured into aqueous sodium hydrogen carbonate (30 mL). Extraction with ethyl acetate/tetrahydrofuran (2:1, 2×30 mL), drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil. The oil was purified by column chromatography (12 g, silica, Combiflash, dichloromethane to 80:20 dichloromethane/methanol) to afford the title compound (0.053 g, 36%) as a yellow solid:

後処理

  1. extractionExtraction with ethyl acetate/tetrahydrofuran (2:1, 2×30 mL)
  2. dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure
  3. customgave an oil
  4. customThe oil was purified by column chromatography (12 g, silica, Combiflash, dichloromethane to 80:20 dichloromethane/methanol)

出典と根拠

ORDレコード
ord-bd603f2baa414cc783da7f502decb352
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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