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Triethylamine → 1-((tert-Butyldimethylsilyl)oxy)-3-(5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propan-2-yl methanesulfonate

HRID 2201208
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Reaktionsgleichung

Reaktionsgleichung von HRID 2201208
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=[O:4])=[O:3].C(N(CC)CC)C.[Si:17]([O:24][CH2:25][CH:26](O)[CH2:27][N:28]1[C:36]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[CH:38]=2)=[C:35]2[C:30]([N:31]([CH3:47])[C:32](=[O:46])[N:33]([CH3:45])[C:34]2=[O:44])=[CH:29]1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>ClCCCl.CN(C1C=CN=CC=1)C.O>[CH3:1][S:2]([O:5][CH:26]([CH2:27][N:28]1[C:36]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[CH:38]=2)=[C:35]2[C:30]([N:31]([CH3:47])[C:32](=[O:46])[N:33]([CH3:45])[C:34]2=[O:44])=[CH:29]1)[CH2:25][O:24][Si:17]([C:20]([CH3:23])([CH3:21])[CH3:22])([CH3:18])[CH3:19])(=[O:4])=[O:3]
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Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 867234486-(3-((tert-Butyldimethylsilyl)oxy)-2-hydroxypropyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Produkt 1

HCID 867234491-((tert-Butyldimethylsilyl)oxy)-3-(5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propan-2-yl methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 111,2-DichloroethaneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

Methanesulfonic anhydride (0.679 g, 3.90 mmol) in 1,2-dichloroethane (3.0 mL) was added dropwise to a solution of DMAP (0.016 g, 0.130 mmol), triethylamine (0.544 ml, 3.90 mmol) and 6-(3-((tert-butyldimethylsilyl)oxy)-2-hydroxypropyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (0.6 g, 1.300 mmol) in 1,2-dichloroethane (10 mL) at 0° C. The mixture was warmed to room temperature and stirred for 2 hours, then diluted with water (10 mL). The phases were separated and the aqueous phase was extracted with DCM (3×10 mL). The combined organic extracts were dried over magnesium sulfate and evaporated under vacuum to afford the title compound.

Aufarbeitung

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with DCM (3×10 mL)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c0dbe5a093a9471ca6ade70bbd725e12
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09359381B2

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