Sodium ethoxide → HCID 178493101, compound

HRID 1930546Notes

Reaction equation

O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH:3]1[C:15]([O:17]C)=O.[O-]CC.[Na+].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([NH:37][C:38]([NH2:40])=[NH:39])[CH:28]=[CH:29][C:30]=1[N:31]1[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]1>C(O)C>[OH:17][C:15]1[C:3]2[CH2:4][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:6][CH2:7][C:2]=2[N:40]=[C:38]([NH:37][C:27]2[CH:28]=[CH:29][C:30]([N:31]3[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]3)=[C:25]([O:24][CH3:23])[CH:26]=2)[N:39]=1

Participants

Conditions

Temperature: 100 °C

Procedure

In a microwave vial was 1-tert-butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate (0.577 g, 2.24 mmol, Example 7c), Sodium ethoxide (0.153 g, 2.24 mmol), and 1-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)guanidine (0.55 g, 2.24 mmol) added in ethanol (10 mL) to give a suspension. The reaction was heated in the microwave oven for 20 min at 100° C. Solvent was evaporated under reduced pressure. The crude was dissolved in minimal volume of EtOH and few drops of water added to allow the product to precipitate. The precipitated product was filtered and dried to give tert-butyl 4-hydroxy-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.400 g, 39.4%). MS (ESI+)/(ESI−) m/z 453/450

Workup

customto give a suspension
customSolvent was evaporated under reduced pressure
dissolutionThe crude was dissolved in minimal volume of EtOH and few drops of water
additionadded
customto precipitate
filtrationThe precipitated product was filtered
customdried

Sources & evidence

ORD record: ord-7f529275e6cc436a965e34195754e558
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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