Water → 3-chloro-5-methyl-7-neopentyl-2-(4-(pyridin-4-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 57659

반응식

HRID 57659 반응식
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[CH:9][N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=4)=[CH:15][CH:14]=3)[N:11]=[C:5]2[N:4]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:3]1=[O:30].[Cl:31]C(Cl)(Cl)C(Cl)(Cl)Cl.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.O>C(Cl)Cl.C1COCC1>[Cl:31][C:9]1[N:10]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[CH:17][CH:18]=2)[N:11]=[C:5]2[C:6]=1[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:30])[N:4]2[CH2:25][C:26]([CH3:27])([CH3:29])[CH3:28]

참가 물질

7

반응물 4

HCID 962WaterHCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 700974725-methyl-7-neopentyl-2-(4-(pyridin-4-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

생성물 1

HCID 700953303-chloro-5-methyl-7-neopentyl-2-(4-(pyridin-4-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione수율 92.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

5-methyl-7-neopentyl-2-(4-(pyridin-4-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (500 mg, 1.24 mmol) and hexachloroethane (587 mg, 2.48 mmol) are dissolved in 8 mL of methylene chloride, and then 1.0 M LiHMDS (2.48 mL, 2.48 mmol) in THF is added dropwise. After the reaction mixture is stirred at room temperature for 10 min, 100 mL of deionized water is added, and then extracted with methylene chloride four times (30 mL×4). The combined organic phase is dried over anhydrous sodium sulfate. After filtration, the filtrate is evaporated to dryness to give 500 mg of crude product as brown solids, which is used in the next step without further purification. MS (ESI) m/z 438.2 [M+H]+.

후처리

  1. extractionextracted with methylene chloride four times (30 mL×4)
  2. dry with materialThe combined organic phase is dried over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. customthe filtrate is evaporated to dryness

출처 및 근거

ORD 기록
ord-4e697967616d4cdf8d5d6ee1edca4796
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434730B2

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