4-Aminopyridine → 2-(5-Bromo-2-fluorophenyl)-4-(4-pyridylamino)pteridine

HRID 928263

반응식

HRID 928263 반응식
C(N(CC)CC)C.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([F:26])=[C:13]([C:15]2[NH:24][C:23](=O)[C:22]3[C:17](=[N:18][CH:19]=[CH:20][N:21]=3)[N:16]=2)[CH:14]=1.[NH2:27][C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([F:26])=[C:13]([C:15]2[N:24]=[C:23]([NH:27][C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[C:22]3[C:17](=[N:18][CH:19]=[CH:20][N:21]=3)[N:16]=2)[CH:14]=1

참가 물질

6

반응물 4

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 2724699PyBOPHCID 1361099582-(5-Bromo-2-fluoro-phenyl)-3H-pteridin-4-one

생성물 1

HCID 119622182-(5-Bromo-2-fluorophenyl)-4-(4-pyridylamino)pteridine수율 32.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (1.04 mL, 7.17 mmol) was added to a solution of 2-(5-bromo-2-fluoro-phenyl)pteridin-4-one 104 (800 mg, 2.49 mmol), 4-aminopyridine (469 mg, 4.98 mmol) and PyBOP (2.59 g, 4.98 mmol) in CH2Cl2. After 12 h, the reaction mixture was partitioned between CH2Cl2/Petroleum ether (2:1, 300 mL) and ice-cold 1N HCl (300 mL). The pH of the water phase was adjust to 12 with conc. NaOH and extracted with AcOEt, dried (Na2SO4) and evaporated. The residue was triturated in CH2Cl2/Petroleum ether (2:1, 15 mL), filtered off, and washed with ether. The product was purified by column chromatography (AcOEt/CH2Cl2/MeOH, 5:4:1) to give 325 mg of the title product 1 as a yellow powder (LCMS analysis).

후처리

  1. customthe reaction mixture was partitioned between CH2Cl2/Petroleum ether (2:1, 300 mL) and ice-cold 1N HCl (300 mL)
  2. extractionextracted with AcOEt
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was triturated in CH2Cl2/Petroleum ether (2:1, 15 mL)
  6. filtrationfiltered off
  7. washwashed with ether
  8. customThe product was purified by column chromatography (AcOEt/CH2Cl2/MeOH, 5:4:1)

출처 및 근거

ORD 기록
ord-e424538959524fd3a03095ac2cf1a4bf
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290502B2

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