N-Fluorobenzenesulfonimide → 4-Chloro-5-fluoro-7H-pyrrolo(2,3-d)pyrimidine

HRID 221293

반응식

HRID 221293 반응식
[Cl:1][C:2]1[C:3]2[C:10](Br)=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Li]CCCC.[B-](F)(F)(F)[F:18].[B-](F)(F)(F)F.C1[N+]2(O)CC[N+](F)(CC2)C1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)F)(=O)=O)=CC=1>C1COCC1>[Cl:1][C:2]1[C:3]2[C:10]([F:18])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

참가 물질

6

반응물 4

HCID 588007N-FluorobenzenesulfonimideHCID 27373291-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)HCID 53807105-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidineHCID 178418339Butyllithium

생성물 1

HCID 113212244-Chloro-5-fluoro-7H-pyrrolo(2,3-d)pyrimidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 4-chloro-5-bromo-7H-pyrrolo[2,3-d]pyrimidine (800 mg, 3.45 mmol) in THF (50 mL) at −78° C. was treated with n-BuLi (1.6 M in hexane, 2.2 eq, 7.6 mmol, 4.7 mL) dropwise, and stirred for 30 minutes at the same temperature. The mixture was treated with a solution of ACCUFLUOR® NFSi (2.0 eq, 7 mmol, 2.2 g) in THF (10 mL). The reaction mixture was allowed to warm to room temperature, was stirred for 10 h, and then concentrated to dryness. The residue was dissolved in EtOAc (100 mL), washed with water (3×15 mL) and brine (15 mL), dried with Na2SO4, and purified by reverse phase HPLC (10×250 mm C18 Luna column, 4.7 mL/min, 10-90% acetonitrile in water over 20 min) to provide intermediate compound 1. ESI-MS m/z=172.1 (MH+).

후처리

  1. stirringwas stirred for 10 h
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was dissolved in EtOAc (100 mL)
  4. washwashed with water (3×15 mL) and brine (15 mL)
  5. dry with materialdried with Na2SO4
  6. custompurified by reverse phase HPLC (10×250 mm C18 Luna column, 4.7 mL/min, 10-90% acetonitrile in water over 20 min)

출처 및 근거

ORD 기록
ord-b2208915e10544eab075d3ea59de5883
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207153B2

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