Reaktion #79754

Reaktionsgleichung

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

Pyridine

2-pyridinecarbonyl chloride hydrochloride

→

N5-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]-1,3-dimethyl-1H-5-pyrazolecarboxamide

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

5-(4-Amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (80mg, 0.236 mmol) was dissolved in dichloromethane (2.0 mL). Pyridine (2.0 mL) was added followed by 2-pyridinecarbonyl chloride hydrochloride (63 mg, 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 N5-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]-1,3-dimethyl-1H-5-pyrazolecarboxamide (30 mg, 0.065 mmol). 1H NMR (CDCl3-d) δ 2.11 (m, 4H), 2.32 (s, 3H), 3.66 (m, 2H), 3.99 (s, 3H), 4.13(m, 2H), 4.17 (s, 3H), 4.99 (m, 1H), 5.22 (bs, 2H), 6.46 (s, 1H), 7.03 (s, 1H), 7.07 (s, 1H), 7.12 (d, J=8.2 Hz, 1H), 8.33 (2, 2H), 8.49(d, J=8.2 Hz, 1H). LC/MS: MH+=462.

Quelle