Réaction #79757

Équation de réaction

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

dichloromethane

Pyridine

3-phenylpropanoyl chloride

→

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

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 (50 mg, 0.147 mmol) was dissolved in dichloromethane (1.5 mL). Pyridine (1.5 mL) was added followed by 3-phenylpropanoyl chloride (37 mg, 0.221 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]-2,2-dimethylpropanamide (7 mg, 0.015 mmol). 1H NMR (CDCl3-d) δ 2.07 (m, 4H), 2.75 (m, 2H), 3.09 (m,2H), 3.65 (m, 2H), 3.88 (s, 3H), 4.13(m, 2H), 4.96 (m, 1H), 5.97 (bs, 2H), 6.93 (s, 1H), 7.05 (m, 2H), 7.26 (m, 5H), 7.70 (s, 1H), 8.24 (s, 1H), 8.46 (d, J=8.2 Hz, 1H). LC/MS: MH+=472.

Source