Sodium ethoxide → 7-Benzyl-8-methyl-3,5,6,8-tetrahydropyrido[3,4-d]pyrimidin-4-one

HRID 45081Notes

Reaction equation

C[O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]([CH3:18])[C:6]1=O)=O.Cl.[CH:21]([NH2:23])=[NH:22].CC[O-].[Na+]>CCO>[CH2:11]([N:8]1[CH2:9][CH2:10][C:5]2[C:3](=[O:2])[NH:23][CH:21]=[N:22][C:6]=2[CH:7]1[CH3:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1-benzyl-2-methyl-3-oxo-piperidine-4-carboxylic acid methyl ester (1.0 g, 3.9 mmol), formamidine hydrochloride (930 mg, 11.6 mmol), and EtOH (6 mL) is treated with NaOEt solution (5.5 mL, 13.57 mmol, 21% w/w in EtOH) and the reaction is stirred at 90° C. for 2 h. Reaction is concentrated in vacuo after adjusting to pH 6. Residue is via semi-prep HPLC (C18; 10-100% I/H2O with 0.1% NH4OH) to give the title compound. MS (ESI) m/z 256.0 (M+1).

Workup

customReaction
concentrationis concentrated in vacuo

Sources & evidence

ORD record: ord-fb4be5184a514e069f2c5ab7e30c45b6
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541432B2

Reaction notes

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