Sodium ethoxide → Ammonium Hydroxide

HRID 453149Notes

Reaction equation

HRID 453149 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>[NH4+:8].[OH-:2].[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

6

Reactant 3

HCID 2723922Sodium ethoxideHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 67423405Methyl 1-benzyl-2-methyl-3-oxopiperidine-4-carboxylate

Product 2

HCID 14923Ammonium HydroxideYield 0.1%HCID 1361587847-Benzyl-8-methyl-3,5,6,8-tetrahydropyrido[3,4-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. customReaction
  2. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-be658c9126394dbbb9762f6ae97a882d
Source dataset
uspto-grants-2013_07
Patent number
US08492393B2

Reaction notes

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