Reaktion #3539

Reaktionsgleichung

tert-butyl isocyanate

6-(2,6-dichlorophenyl)-N2 -(3-morpholin-4-yl-propyl)-pyrido[2,3-d]pyrimidine-2,7-diamine

6-(2,6-Dichlorophenyl)-N2 -(3-morpholin-4-yl-propyl)-pyrido[2,3-d]pyrimidine-2,7-diamine

sodium hydride

→

title compound

Ausbeute 79.8%

1-tert-Butyl-3-[6-(2,6-dichlorophenyl)-2-(3-morpholin-4-yl-propylamino)-pyrido[2,3-d]pyrimidin-7-yl]-urea

Ausbeute 79.8%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter approximately 4 hours
2. 2
   Sonstigethe solvent was removed in vacuo
3. 3
   SonstigeThe residue was partitioned between ethyl acetate and water
4. 4
   WaschenThe aqueous layer was washed several times with ethyl acetate
5. 5
   Trocknendried with magnesium sulfate
6. 6
   Einengenconcentrated in vacuo

Vorschrift

To a solution of 6-(2,6-dichlorophenyl)-N2 -(3-morpholin-4-yl-propyl)-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 58 in DMF (15 mL) was added one equivalent of 60% sodium hydride suspension (0.92 g). After stirring for approximately 1 hour at room temperature, one equivalent of tert-butyl isocyanate (0.230 g) was added, and the reaction was monitored by thin layer chromatography. After approximately 4 hours, the solvent was removed in vacuo. The residue was partitioned between ethyl acetate and water. The aqueous layer was washed several times with ethyl acetate. The ethyl acetate layers were combined, dried with magnesium sulfate, and concentrated in vacuo. Chromatography of the residue on silica gel using ethyl acetate followed by ethyl acetate:ethanol:triethylamine (18:2:1) gave 0.98 g of the title compound 1-tert-butyl-3-[6-(2,6-dichlorophenyl)-2-(3-morpholin-4-yl-propylamino)-pyrido[2,3-d]pyrimidin-7-yl]-urea, CIMS (1% NH3 in CH4): 532=M+ +H, 531=M+,433, 84 (Base); mp 236°-240° C.

Quelle