Sodium hydride → 6-[2-(Pyridin-4-yloxy)-ethoxy]-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl oxime

HRID 1853359노트

반응식

HRID 1853359 반응식
[H-].[Na+].[C:3]([O:7][N:8]=[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:19])[CH:17]=2)[O:12][C:11]([C:20]2[N:25]=[CH:24][N:23]3[CH:26]=[CH:27][CH:28]=[C:22]3[CH:21]=2)=[CH:10]1)([CH3:6])([CH3:5])[CH3:4].Cl[CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1.C1OCCOCCOCCOCCOC1>CN1C(=O)CCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>[C:3]([O:7][N:8]=[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH2:30][CH2:31][O:32][C:33]3[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=3)[CH:17]=2)[O:12][C:11]([C:20]2[N:25]=[CH:24][N:23]3[CH:26]=[CH:27][CH:28]=[C:22]3[CH:21]=2)=[CH:10]1)([CH3:6])([CH3:4])[CH3:5]

참가 물질

8

반응물 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 226249214-(2-Chloroethoxy)pyridineHCID 866730736-Hydroxy-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl-oxime

생성물 1

HCID 866731206-[2-(Pyridin-4-yloxy)-ethoxy]-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl oxime수율 42%

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 13387N-methyl-2-pyrrolidone용매3회HCID 25517Ammonium Chloride용매

실험 절차

To a mixture of sodium hydride 60% in oil (11.5 mg, 0.28 mmol) in NMP (0.5 ml) was added at 0° C. a solution of 6-hydroxy-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl-oxime (example 81A) (100 mg, 0.28 mmol) in NMP (0.5 ml). After 1 hour at room temperature, a solution of 4-(2-Chloro-ethoxy)-pyridine (103 mg, 042 mmol), tetrabutyl ammonium iodide (53 mg, 0.14 mmol), 15-crown-5 (63 mg, 0.28 mmol) in NMP (0.5 ml) was added at 0° C. After stirring at room temperature for 24 hours, the reaction mixture was diluted with a saturated solution of ammonium chloride and extracted with ethyl acetate. The organic layers were washed with a saturated solution of ammonium chloride, water, brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography over silica gel (gradient cyclohexane/ethyl acetate: 0-70%) to yield the title compound (54 mg, 42%) as a yellow solid.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layers were washed with a saturated solution of ammonium chloride, water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography over silica gel (gradient cyclohexane/ethyl acetate: 0-70%)

출처 및 근거

ORD 기록
ord-eb87c7a7e2ea43ddadb2f519dd9b9527
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962627B2

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