Dimethyl Disulfide → 2-(4-(1H-1,2,4-triazol-1-yl)benzyl)-5-methyl-3-(methylthio)-7-neopentyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 535889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 535889
[N:1]1([C:6]2[CH:29]=[CH:28][C:9]([CH2:10][N:11]3[CH:19]=[C:18]4[C:13]([N:14]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:15](=[O:22])[N:16]([CH3:21])[C:17]4=[O:20])=[N:12]3)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.[CH3:30][S:31]SC.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C(Cl)Cl.C1COCC1>[N:1]1([C:6]2[CH:29]=[CH:28][C:9]([CH2:10][N:11]3[C:19]([S:31][CH3:30])=[C:18]4[C:13]([N:14]([CH2:23][C:24]([CH3:26])([CH3:25])[CH3:27])[C:15](=[O:22])[N:16]([CH3:21])[C:17]4=[O:20])=[N:12]3)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Komponenten

6

Edukt 3

HCID 12232Dimethyl DisulfideHCID 2733832Lithium HexamethyldisilazideHCID 667661342-(4-(1H-1,2,4-triazol-1-yl)benzyl)-5-methyl-7-neopentyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Produkt 1

HCID 462094022-(4-(1H-1,2,4-triazol-1-yl)benzyl)-5-methyl-3-(methylthio)-7-neopentyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-(4-(1H-1,2,4-triazol-1-yl)benzyl)-5-methyl-7-neopentyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (52 mg, 0.132 mmol) and methyl disulfide (12 μL, 0.13 mmol) are dissolved in 2 mL of anhydrous CH2Cl2, and then 1.0 M LiHMDS (190 μL, 0.19 mmol) in THF is added dropwise. The reaction mixture is stirred at room temperature for 30 min, and then quenched with saturated ammonium chloride aqueous solution. After routine workup, the obtained crude product is purified by silica gel column chromatography to give pure product as off-white solids. MS (ESI) m/z 440.2 [M+H]+.

Aufarbeitung

  1. customquenched with saturated ammonium chloride aqueous solution
  2. customAfter routine workup, the obtained crude product
  3. customis purified by silica gel column chromatography
  4. customto give pure product as off-white solids

Quellen und Nachweise

ORD-Eintrag
ord-abbbf64941ff4d9fb3617660a8270c26
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859564B2

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