Réaction #3539

Équation de réaction

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

Rendement 79.8%

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

Rendement 79.8%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   workup.WAITAfter approximately 4 hours
2. 2
   Autrethe solvent was removed in vacuo
3. 3
   AutreThe residue was partitioned between ethyl acetate and water
4. 4
   LavageThe aqueous layer was washed several times with ethyl acetate
5. 5
   Séchagedried with magnesium sulfate
6. 6
   Concentrationconcentrated in vacuo

Mode opératoire

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.

Source