Potassium Phosphate, Tribasic → 6-(1,4-Diazabicyclo[3.2.2]nonan-4-yl)-3-methylthieno[2,3-d]pyrimidin-4(3H)-one

HRID 77409

Reaktionsgleichung

Br[C:2]1[S:12][C:5]2[N:6]=[CH:7][N:8]([CH3:11])[C:9](=[O:10])[C:4]=2[CH:3]=1.N1CCC[C@H]1C(O)=O.[N:21]12[CH2:29][CH2:28][CH:25]([CH2:26][CH2:27]1)[NH:24][CH2:23][CH2:22]2.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CS(C)=O.CO.[Cu]I.C(O)(=O)C>[N:21]12[CH2:29][CH2:28][CH:25]([CH2:26][CH2:27]1)[N:24]([C:2]1[S:12][C:5]3[N:6]=[CH:7][N:8]([CH3:11])[C:9](=[O:10])[C:4]=3[CH:3]=1)[CH2:23][CH2:22]2

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A mixture of 6-bromo-3-methylthieno[2,3-d]pyrimidin-4(3H)-one (70 mg, 0.28 mmol), copper(I) iodide (13.6 mg, 0.071 mmol), L-proline (16.4 mg, 0.143 mmol), 1,4-diazabicyclo[3.2.2]nonane (54.1 mg, 0.428 mmol) and potassium phosphate (132 mg, 0.571 mmol) in DMSO (1 mL) was heated at 90° C. in a sealed vessel for 3 days. The reaction was acidified with acetic acid, diluted with methanol and purified on a scx cartridge (1 g), further purified by acid prep HPLC, passed through a scx cartridge (500 mg) and evaporated to dryness to afford 6-(1,4-Diazabicyclo[3.2.2]nonan-4-yl)-3-methylthieno[2,3-d]pyrimidin-4(3H)-one (1.8 mg, 0.006 mmol).

Aufarbeitung

custompurified on a scx cartridge (1 g)
customfurther purified by acid prep HPLC
customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag: ord-577e0f506d014acb9049cec4c76da0ea
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08841289B2

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