Potassium Carbonate → 2-(Methylthio)-4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyrimidine

HRID 2175244노트

반응식

HRID 2175244 반응식
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[C:15](=O)([O-])[O-].[K+].[K+].BrC[C:23]1[CH:24]=[N:25][C:26]([S:29][CH3:30])=[N:27][CH:28]=1>CN(C=O)C.CCOC(C)=O>[CH3:30][S:29][C:26]1[N:25]=[C:24]([CH2:15][N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]3)[CH:10]=[N:11]2)[CH:23]=[CH:28][N:27]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 60209911HCID 60209911, 화합물

생성물 1

HCID 709823642-(Methylthio)-4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyrimidine수율 70%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.5 g, 2.58 mmol), potassium carbonate (0.356 g, 2.58 mmol) and 5-(bromomethyl)-2-(methylthio)pyrimidine (30% in THF, 2.070 g, 2.83 mmol) in DMF (5 mL) was stirred at room temperature for 14 h. After this time, the reaction mixture was diluted with EtOAc, washed with saturated sodium bicarbonate, dried over anhydrous MgSO4, filtered, and concentrated. The resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes) to afford the title compound (0.6 g, 70% yield) as a light yellow solid. LCMS, [M+H]+=333.2. 1H NMR (400 MHz, CDCl3) δ 8.43 (d, J=5.1 Hz, 1H), 7.87 (s, 1H), 7.81 (s, 1H), 6.49 (d, J=5.1 Hz, 1H), 5.36 (s, 2H), 2.56 (s, 3H), 1.33 (s, 12H).

후처리

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-b1135a91db0e49a8857af47de88e6a68
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062028B2

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