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Sodium Carbonate → 2-bromo-4-(cyclopropylmethyl)pyrido[2,3-b]pyrazin-3(4H)-one

HRID 1924464
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HRID 1924464 반응식
[CH:1]1([CH2:4][N:5]2[C:10](=[O:11])[C:9](O)=[N:8][C:7]3[CH:13]=[CH:14][CH:15]=[N:16][C:6]2=3)[CH2:3][CH2:2]1.P(Br)(Br)([Br:19])=O.C(=O)([O-])[O-].[Na+].[Na+]>ClC(Cl)C>[Br:19][C:9]1[C:10](=[O:11])[N:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[C:6]2[N:16]=[CH:15][CH:14]=[CH:13][C:7]=2[N:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 24613Phosphorus oxybromideHCID 1785169094-(cyclopropylmethyl)-2-hydroxypyrido[2,3-b]pyrazin-3(4H)-one

생성물 1

HCID 581031982-bromo-4-(cyclopropylmethyl)pyrido[2,3-b]pyrazin-3(4H)-one수율 66.5%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

700 mg (3.22 mM) of 4-(cyclopropylmethyl)-2-hydroxypyrido[2,3-b]pyrazin-3(4H)-one and 972.3 mg (3.22 mM) of phosphorus oxybromide at 95% in 10 ml of dichloroethane were refluxed for 16H under stirring. The reaction mixture was then basified with an aqueous solution of sodium carbonate and the aqueous layer was extracted with dichloromethane. The organic layer was separated, washed with water, dried on anhydrous sodium sulfate and the solvent was removed under vacuum. The compound was further purified by silica gel column chromatography, using dichloromethane as eluant, to give, after evaporation, 650 mg of 2-bromo-4-(cyclopropylmethyl)pyrido[2,3-b]pyrazin-3(4H)-one as a white solid. Yield: 66.5%.

후처리

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. customthe solvent was removed under vacuum
  6. customThe compound was further purified by silica gel column chromatography
  7. customto give
  8. customafter evaporation, 650 mg of 2-bromo-4-(cyclopropylmethyl)pyrido[2,3-b]pyrazin-3(4H)-one as a white solid

출처 및 근거

ORD 기록
ord-13a5bb30147e42ff82c60a77c49588ce
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08178556B2

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