Hexachloroethane → 5-chloro-1-isobutyl-6-(4-methoxybenzyl)-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2205655노트

반응식

HRID 2205655 반응식
[CH2:1]([N:5]1[C:10]2=[CH:11][N:12]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:13]=[C:9]2[C:8](=[O:23])[N:7]([CH3:24])[C:6]1=[O:25])[CH:2]([CH3:4])[CH3:3].[Cl:26]C(Cl)(Cl)C(Cl)(Cl)Cl.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Cl:26][C:13]1[N:12]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH:11]=[C:10]2[C:9]=1[C:8](=[O:23])[N:7]([CH3:24])[C:6](=[O:25])[N:5]2[CH2:1][CH:2]([CH3:4])[CH3:3]

참가 물질

5

반응물 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 102467011-isobutyl-6-(4-methoxybenzyl)-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

생성물 1

HCID 674146965-chloro-1-isobutyl-6-(4-methoxybenzyl)-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione수율 120.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

1-isobutyl-6-(4-methoxybenzyl)-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (1.88 g, 5.5 mmol) and hexachloroethane (6.5 g, 26.5 mmol) are dissolved in anhydrous THF (3 mL), and then 1.0 M LiHMDS in THF (11 mL, 11 mmol) is added dropwise over 2 hours. The reaction mixture is stirred at room temperature for an hour, and then quenched with saturated ammonium chloride aqueous solution. The mixture is poured into cold water (100 mL), and then extracted with ethyl acetate three times. The combined organic phase is dried with anhydrous sodium sulfate. After filtration, the filtrate is evaporated to dryness to give 2.5 g of crude product as light brown solids, which is used in the next step without further purification. MS (ESI) m/z 376.1 [M+H]+.

후처리

  1. customquenched with saturated ammonium chloride aqueous solution
  2. additionThe mixture is poured into cold water (100 mL)
  3. extractionextracted with ethyl acetate three times
  4. dry with materialThe combined organic phase is dried with anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe filtrate is evaporated to dryness

출처 및 근거

ORD 기록
ord-80afaa44a971469ebf19dcbb54d6c233
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371327B2

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