Réaction #79752

Équation de réaction

5-(4-Amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Pyridine

benzoyl chloride

→

N1-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]benzamide

Rendement 61.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autrethe solvent was removed
2. 2
   workup.DISSOLUTIONthe residue was dissolved in 1 ml DMSO
3. 3
   workup.ADDITIONmethanol (1 mL) was added
4. 4
   Autreprecipitate was formed
5. 5
   FiltrationThe solid was collected by filtration

Mode opératoire

5-(4-Amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (80 mg, 0.236 mmol) was dissolved in dichloromethane (2.0 mL). Pyridine (2.0 mL) was added followed by benzoyl chloride (41 uL, 0.353 mmol). After stirring at room temperature for 2 hours, the solvent was removed and the residue was dissolved in 1 ml DMSO, methanol (1 mL) was added and precipitate was formed. The solid was collected by filtration to give N1-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]benzamide (64 mg, 0.144 mmol). 1H NMR (CDCl3-d) δ 2.12 (m, 4H), 3.67 (m, 2H), 3.99 (s, 3H), 4.17(m, 2H), 4.99 (m, 1H), 7.03(s, 1H), 7.04 (s, 1H), 7.14 (d, J=8.2 Hz, 1H), 7.53 (m, 3H), 7.94(d, J=7.8 Hz, 1H), 8.33 (s, 1H), 8.58 (s, 1H), 8.63 (d, J=8.2 Hz, 1H). LC/MS: MH+=444.

Source