Potassium Carbonate → 4-chloro-1-methyl-3-[2-methyl-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-phenoxymethyl]-1H-pyrazolo[3,4-d]pyrimidine

HRID 2426119노트

반응식

HRID 2426119 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[N:9]=2)=[CH:4][C:3]=1[OH:14].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]1[C:31]2[C:26](=[N:27][CH:28]=[N:29][C:30]=2[Cl:32])[N:25]([CH3:33])[N:24]=1>CN(C)C=O>[Cl:32][C:30]1[N:29]=[CH:28][N:27]=[C:26]2[N:25]([CH3:33])[N:24]=[C:23]([CH2:22][O:14][C:3]3[CH:4]=[C:5]([C:8]4[O:12][N:11]=[C:10]([CH3:13])[N:9]=4)[CH:6]=[CH:7][C:2]=3[CH3:1])[C:31]=12

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 575815813-bromomethyl-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidineHCID 575815912-Methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)phenol

생성물 1

HCID 252270084-chloro-1-methyl-3-[2-methyl-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-phenoxymethyl]-1H-pyrazolo[3,4-d]pyrimidine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 2-methyl-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-phenol (72.0 mg, 0.0.379 mmol) and potassium carbonate (64.2 mg, 0.455 mmole) in dimethylformamide was stirred at room temperature for 30 minutes before 3-bromomethyl-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine (89.8 mg, 0.280 mmol, Example 5) was added. The reaction was stirred at room temperature overnight and then concentrated under reduced pressure to remove dimethylformamide. The residue was dissolved in ethyl acetate, washed with water, dried and concentrated. The crude product was purified by flash chromatography (silica gel, hexanes-ethyl acetate, 90/10 to 60/40) to give pure 4-chloro-1-methyl-3-[2-methyl-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-phenoxymethyl]-1H-pyrazolo[3,4-d]pyrimidine as a white solid. (Yield 41.0 mg).

후처리

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. customto remove dimethylformamide
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography (silica gel, hexanes-ethyl acetate, 90/10 to 60/40)

출처 및 근거

ORD 기록
ord-cde02f4e8c7c4158b3b803e4eb974189
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968554B2

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