Sodium Carbonate → 5-(4-methoxybenzyloxy)-3-methyl-7-(4-morpholinophenyl)pyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1023318Notes

Reaction equation

Cl[C:2]1[N:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:9]2[C:8](=[O:22])[N:7]([CH3:23])[CH:6]=[N:5][C:4]=2[CH:3]=1.[O:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][C:33](B3OC(C)(C)C(C)(C)O3)=[CH:32][CH:31]=2)[CH2:26][CH2:25]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][O:12][C:10]2[C:9]3[C:8](=[O:22])[N:7]([CH3:23])[CH:6]=[N:5][C:4]=3[CH:3]=[C:2]([C:33]3[CH:32]=[CH:31][C:30]([N:27]4[CH2:26][CH2:25][O:24][CH2:29][CH2:28]4)=[CH:35][CH:34]=3)[N:11]=2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 7-chloro-5-(4-methoxybenzyloxy)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (750 mg, 2.26 mmol) in 1,4-dioxane (11 mL) were added 4-morpholinophenylboronic acid pinacol ester (654 mg, 2.26 mmol), 2M aqueous Na2CO3 solution (3.39 mL, 6.78 mmol), and Pd(dppf)2Cl2 (36.9 mg, 0.045 mmol). The reaction mixture was purged with N2 and heated at 140° C. by a microwave reactor for 15 minutes. The mixture was then cooled, quenched with H2O (100 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic layer was dried over MgSO4 and evaporated under reduced pressure to afford crude 5-(4-methoxybenzyloxy)-3-methyl-7-(4-morpholinophenyl)pyrido[4,3-d]pyrimidin-4(3H)-one.

Workup

customThe reaction mixture was purged with N2
temperatureThe mixture was then cooled
customquenched with H2O (100 mL)
extractionextracted with CH2Cl2 (3×50 mL)
dry with materialThe combined organic layer was dried over MgSO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-a86b379a273b41e59f6b27681b101ee3
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722692B2

Reaction notes

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