Reaktion #359607

Reaktionsgleichung

6-Bromo-8-cyclopentyl-2-methanesulfinyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

4-(6-Amino-pyridin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester

→

4-[6-(6-Bromo-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester

Ausbeute 13.0%

Lösungsmittel

CH2Cl2

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched by the addition of succinic anhydride (0.2 g)
2. 2
   Temperaturto cool
3. 3
   Sonstigegiving a solid
4. 4
   Filtrationfiltered
5. 5
   Sonstigeto give a white solid
6. 6
   WaschenThe filtrate was washed with saturated aqueous sodium bicarbonate
7. 7
   Trocknensaturated aqueous sodium chloride and dried over anhydrous magnesium sulfate
8. 8
   SonstigeThe crude product was purified by silica gel chromatography
9. 9
   Wascheneluting with 75% ethyl acetate

Vorschrift

6-Bromo-8-cyclopentyl-2-methanesulfinyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (0.2 g, 0.54 mmol, prepared according to Example 5 in WO 01/70741) and 4-(6-Amino-pyridin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.6 g, 2.16 mmol) were combined in toluene (3 mL) and heated to 110° C. overnight. The reaction was quenched by the addition of succinic anhydride (0.2 g) and allowed to cool giving a solid. This solid was suspended in CH2Cl2 and filtered to give a white solid. The filtrate was washed with saturated aqueous sodium bicarbonate then saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The crude product was purified by silica gel chromatography eluting with 75% ethyl acetate:25% hexanes to provide 4-[6-(6-Bromo-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.04 g, 13%). MS (APCI) M++1: Calc'd, 584.19. Found, 584.1.

Quelle