4-Pyridinemethanamine → 5-((pyridin-4-yl)methylamino)-7-chloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1805757Notes

Reaction equation

Cl[C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH3:13])[CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([Cl:14])[N:3]=1.[N:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH2:22])=[CH:17][CH:16]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[N:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:22][C:2]2[C:11]3[C:10](=[O:12])[N:9]([CH3:13])[CH:8]=[N:7][C:6]=3[CH:5]=[C:4]([Cl:14])[N:3]=2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 90 °C

Procedure

5,7-dichloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (200 mg, 0.87 mmol) and (pyridin-4-yl)methanamine (188 mg, 1.74 mmol), DIEA (302 μL, 1.74 mmol) were dissolved in dioxane (5 mL). The reaction mixture was stirred at 90° C. overnight and then cooled to room temperature. The solvent was removed under vacuum and the crude product was purified by silica column chromatography using hexane/ethyl acetate/7N NH3 in methanol (60:33:7) to obtain the yellow 5-((pyridin-4-yl)methylamino)-7-chloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one. 1H NMR (DMSO-d6) δ 9.45 (t, J=6 Hz, 1H), 8.49 (m, 3H), 7.32 (d, J=6H, 2H), 6.68 (s, 1H), 4.73 (d, J=6 Hz, 2H), 3.46 (s, 3H); ESI-MS m/z 302.1 (MH+).

Workup

temperaturecooled to room temperature
customThe solvent was removed under vacuum
customthe crude product was purified by silica column chromatography

Sources & evidence

ORD record: ord-fda4faa12fad4c79abea74f6dad3b251
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354526B2

Reaction notes

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