Sodium Iodide → 7-(3-Chloropyridin-2-yl)-N-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

HRID 971220노트

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HRID 971220 반응식
Cl[C:2]1[C:3]2[CH2:11][CH2:10][N:9]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][N:13]=3)[CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1.[I-].[Na+].I>C(#N)C>[Cl:18][C:17]1[C:12]([N:9]2[CH2:10][CH2:11][C:3]3[C:2]([NH:24][C:23]4[CH:25]=[CH:26][C:20]([F:19])=[CH:21][CH:22]=4)=[N:7][CH:6]=[N:5][C:4]=3[CH2:8]2)=[N:13][CH:14]=[CH:15][CH:16]=1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 97314-FluoroanilineHCID 24841Hydrogen iodideHCID 590214784-Chloro-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

생성물 1

HCID 120043457-(3-Chloropyridin-2-yl)-N-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine수율 42.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
130 °C

실험 절차

4-Chloro-7-(3-chloro-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidine (100 mg, 0.35 mmol) was dissolved in acetonitrile (2 mL). To the mixture was added 4-flouroaniline (0.067 mL, 0.71 mmol), sodium iodide (80 mg, 0.53 mmol) and HI (47%, 0.2 mL). The mixture was heated in a sealed tube at 130° C. for 10 minutes in a Personal Chemistry Microwave (Smith Creator). The solvent was removed under vacuum and the resulting orange residue dissolved in ethyl acetate and washed with saturated sodium bicarbonate and brine. The organic layer was dried over sodium sulphate, filtered and evaporated. The residue was purified by flash chromatography over silica gel using a 0-100% ethyl acetate-hexane gradient to give the product as an off white solid (53 mg).

후처리

  1. customThe solvent was removed under vacuum
  2. dissolutionthe resulting orange residue dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography over silica gel using a 0-100% ethyl acetate-hexane gradient

출처 및 근거

ORD 기록
ord-042d79184818475286e837391415b976
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312330B2

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