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 2363929노트

반응식

HRID 2363929 반응식
[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

참가 물질

6

반응물 4

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

생성물 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)-one수율 46.1%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

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:

후처리

  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)

출처 및 근거

ORD 기록
ord-c69849ac086244bb9f99c72fdfa70fd1
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691828B2

반응 노트

불러오는 중…