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

HRID 1023310Notes

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)[N:3]=1.[O:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24](B3OC(C)(C)C(C)(C)O3)=[CH:23][CH:22]=2)[CH2:17][CH2:16]1.[C:36]([O-:39])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][N:9]1[C:10](=[O:12])[C:11]2[C:2]([C:24]3[CH:23]=[CH:22][C:21]([N:18]4[CH2:17][CH2:16][O:15][CH2:20][CH2:19]4)=[CH:26][CH:25]=3)=[N:3][C:4]([C:24]3[CH:25]=[CH:26][C:21]([N:18]4[CH2:19][CH2:36][O:39][CH2:16][CH2:17]4)=[CH:22][CH:23]=3)=[CH:5][C:6]=2[N:7]=[CH:8]1

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 5,7-dichloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (23.0 mg, 0.10 mmol) in 1,4-dioxane (0.5 mL) were added 4-morpholinophenylboronic acid pinacol ester (57.8 mg, 0.20 mmol), 2M aqueous Na2CO3 solution (150 μL, 0.30 mmol), and a catalytic amount of Pd(PPh3)4. 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 (5 mL) and extracted with ethyl acetate (3×2.5 mL). The combined organic layers were evaporated under vacuo and the residue was purified by preparatory LC/MS to provide the title compound; HPLC-MS calculated for C28H29N5O3 (M+H+) 484.2, found 484.2.

Workup

customThe reaction mixture was purged with N2
temperatureThe mixture was then cooled
customquenched with H2O (5 mL)
extractionextracted with ethyl acetate (3×2.5 mL)
customThe combined organic layers were evaporated under vacuo
customthe residue was purified by preparatory LC/MS

Sources & evidence

ORD record: ord-cabb454fdb4642cbb2dbea37dfec19b3
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722692B2

Reaction notes

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