Toluene → (S)-4-Chloro-N-[1-(4-fluorophenyl)ethyl]-6-(pyridin-3-yl)pyrimidine-2-amine

HRID 1187681노트

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HRID 1187681 반응식
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH3:11])[N:3]=1.O1CCCOB1[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[Cl:8][C:6]1[CH:7]=[C:2]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[N:3]=[C:4]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH3:11])[N:5]=1

참가 물질

9

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 86659372(S)-4,6-Dichloro-N-[1-(4-fluorophenyl)ethyl]pyrimidin-2-amine

생성물 1

HCID 86659381(S)-4-Chloro-N-[1-(4-fluorophenyl)ethyl]-6-(pyridin-3-yl)pyrimidine-2-amine수율 37.9%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

500 mg of (S)-4,6-dichloro-N-[1-(4-fluorophenyl)ethyl]pyrimidine-2-amine (Reference Example 1), 314 mg of 3-(1,3,2-dioxaborinan-2-yl)pyridine, 927 mg of sodium carbonate and 202 mg of tetrakis(triphenylphosphine)palladium were added in turn to a degassed mixed solvent of 15 ml of toluene, 7 ml of ethanol and 10 ml of water, and the mixture was stirred at 110° C. for 3 hours under argon atmosphere. The reaction solution was diluted with ethyl acetate. The solution was washed in turn with water and brine and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 218 mg of the objective compound as white powder.

후처리

  1. washThe solution was washed in turn with water and brine
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-9fd5aca10b844786bbdb5dd3a0ab5253
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673891B2

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