Reaktion #73112

Reaktionsgleichung

EDCI

dimethylamine hydrochloride

HOAt

triethylamine

(R)-1-(8-Cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-pyrazole-4-carboxylic acid

→

title compound

(R)-1-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-N,N-dimethyl-1H-pyrazole-4-carboxamide

Lösungsmittel

DCM

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 0.1 N aqueous HCl
2. 2
   Trocknen1 N aqueous NaOH, dried with Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated under vacuum
5. 5
   Sonstigepurified by preparative HPLC

Vorschrift

(R)-1-(8-Cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-pyrazole-4-carboxylic acid (Example 44, 0.14 g, 0.378 mmol) was dissolved in 2 mL of DCM and EDCI (79 mg, 0.415 mmol), dimethylamine hydrochloride (46 mg, 0.567 mmol), HOAt (5 mg, 0.0379 mmol) and triethylamine (115 mg, 1.13 mmol) were added. The resulting solution was stirred at rt for 48 hours after which the reaction mixture was diluted with DCM and washed with 0.1 N aqueous HCl then 1 N aqueous NaOH, dried with Na2SO4, filtered, concentrated under vacuum and purified by preparative HPLC to give the title compound. 1H NMR (CDCl3) δ: 7.55-7.57 (s, 1H), 7.40-7.51 (m, 2H), 4.26-4.51 (m, 2H), 3.11-3.39 (m, 9H), 1.64-2.18 (m, 10H), and 0.97 ppm (m, 3H); LCMS: 398.1 m/z (M+H)+; ret. Time: 3.267 min (Analytical Method A).

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