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Sodium hydride → 7-bromo-4-(pyrimidin-2-ylmethyl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one

HRID 717047
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반응식

HRID 717047 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][NH:8][C:7](=[O:12])[C:6]=2[CH:13]=1.[H-].[Na+].Cl.Cl[CH2:18][C:19]1[N:24]=[CH:23][CH:22]=[CH:21][N:20]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]([CH2:18][C:19]3[N:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[C:7](=[O:12])[C:6]=2[CH:13]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 200256062-(Chloromethyl)pyrimidine hydrochlorideHCID 601249727-Bromo-2,3,4,5-tetrahydro-1,4-benzoxazepin-5-one

생성물 1

HCID 711834087-bromo-4-(pyrimidin-2-ylmethyl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

7-Bromo-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one (1.0 g, 4.13 mmol) was dissolved in DMF (10 ml) cooled down in a ice/water bath and treated with sodium hydride (60% dispersion) (363 mg, 9.08 mmol) portion wise. After 10 min a solution of 2-(chloromethyl)pyrimidine hydrochloride (813 mg, 4.96 mmol) in DMF (4 ml) was added, the reaction mixture warmed up to room temperature and quenched with 12 mL of water after it was complete. The reaction mixture was extracted with EtOAc and water and the organic phase was dried, evaporated and purified by silica gel chromatography (95% DCM/MeOH) to afford 7-bromo-4-(pyrimidin-2-ylmethyl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one.

후처리

  1. temperaturecooled down in a ice/water bath
  2. customquenched with 12 mL of water after it
  3. extractionThe reaction mixture was extracted with EtOAc and water
  4. customthe organic phase was dried
  5. customevaporated
  6. custompurified by silica gel chromatography (95% DCM/MeOH)

출처 및 근거

ORD 기록
ord-d171abbe95704791ba2fdc9906ac4f6c
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09193694B2

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