Water → 6-(Bromomethyl)thieno[3,2-b]pyrazine

HRID 1184860노트

반응식

HRID 1184860 반응식
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[S:7][C:8]([CH2:10]O)=[CH:9][C:2]=12.P(Br)(Br)[Br:13].O.[OH-].[Na+]>C(Cl)Cl.C1COCC1>[Br:13][CH2:10][C:8]1[S:7][C:3]2[C:2](=[N:1][CH:6]=[CH:5][N:4]=2)[CH:9]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 67125540Thieno[2,3-b]pyrazin-6-ylmethanol

생성물 1

HCID 671255506-(Bromomethyl)thieno[3,2-b]pyrazine수율 63.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of thieno[3,2-b]pyrazin-6-ylmethanol 87 (408 mg, 2.455 mmol) in CH2Cl2 (8 mL) and THF (8 mL) was added phosphorus tribromide (1/166 mL, 12.27 mmol) and stirred overnight at rt. Water was added, alkalized with 2N NaOH and extracted with EtOAc. Organic layer was washed with NaHCO3 (aq) solution, brine, dried and evaporated. Purification by chromatography (CH2CL2) gave pure 6-(bromomethyl)thieno[3,2-b]pyrazine 47 (356 mg, 63%). NMR (400 MHz, CDCl3) 4.80 (s, 2H), 7.71 (s, 1H), 8.49 (d, J=2.3 Hz, 1H), 8.64 (d, J=2.3 Hz, 1H). (m/z)=229 and 231 (M+H)+.

후처리

  1. extractionextracted with EtOAc
  2. washOrganic layer was washed with NaHCO3 (aq) solution, brine
  3. customdried
  4. customevaporated
  5. customPurification by chromatography (CH2CL2)

출처 및 근거

ORD 기록
ord-41b48f1c844b4fc88f92fdcaca56d5da
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669256B2

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