Tetrahydro-4H-pyran-4-one → 6'-(pyridin-4-yl)-2,3,5,6-tetrahydro-1'H-spiro [pyran-4,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one

HRID 2363929ノート

反応式

HRID 2363929 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].[O:16]1[CH2:21][CH2:20][C:19](=O)[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:19]4([CH2:20][CH2:21][O:16][CH2:17][CH2:18]4)[NH:1][C:2]=3[CH:6]=2)=[CH:12][CH:11]=1

参加物

6

反応物 4

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 99208523-Amino-5-(pyridin-4-yl)thiophene-2-carboxamide

生成物 1

HCID 667430106'-(pyridin-4-yl)-2,3,5,6-tetrahydro-1'H-spiro [pyran-4,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one収率 46.1%

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 (0.078 g, 0.36 mmol), tetrahydro-4H-pyran-4-one (0.200 g, 2.00 mmol), p-toluenesulfonic acid monohydrate (0.076 g, 0.40 mmol) and toluene (3.0 mL) was stirred for 2 h at 90° C. The mixture was poured into aqueous sodium hydrogen carbonate (50 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 (0.050 g, 46%) 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-c69849ac086244bb9f99c72fdfa70fd1
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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