Sodium Methoxide → HCID 23452369, compound

HRID 1277917Notes

Reaction equation

HRID 1277917 reaction equation
CO[CH:3](OC)[CH:4]([C:18]#[N:19])[CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[C:8]([O:16][CH3:17])[CH:7]=1.S(O)(O)(=O)=O.[OH:27][CH2:28][CH2:29][NH:30][C:31]([NH2:33])=[NH:32].C[O-].[Na+]>C(O)C>[OH:27][CH2:28][CH2:29][NH:30][C:31]1[N:33]=[C:18]([NH2:19])[C:4]([CH2:5][C:6]2[CH:7]=[C:8]([O:16][CH3:17])[C:9]([O:14][CH3:15])=[C:10]([O:12][CH3:13])[CH:11]=2)=[CH:3][N:32]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 14983720alpha-(Dimethoxymethyl)-3,4,5-trimethoxybenzenepropanenitrileHCID 178513025HCID 178513025, compound

Product 1

HCID 23452369HCID 23452369, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.4 g of α-cyano-β-(3,4,5-trimethoxyphenyl)-propionaldehyde dimethylacetal, 3 g of β-hydroxyethylguanidine sulfate and 1.1 g of sodium methylate in 100 ml of ethanol were refluxed for 5 hours. The ethanol was then distilled off and the residue was dissolved in 100 ml of water. On extracting the solution with chloroform, 3.4 g (50% of theory) of 2-(β-hydroxyethylamino)-4-amino-5-(3,4,5-trimethoxybenzyl)-pyrimidine were obtained, melting at 146° C. after recrystallization from isopropanol.

Workup

  1. distillationThe ethanol was then distilled off
  2. dissolutionthe residue was dissolved in 100 ml of water
  3. extractionOn extracting the solution with chloroform

Sources & evidence

ORD record
ord-cf4f310066054e3686a76fae56ab498a
Source dataset
uspto-grants-1981_07
Patent number
US04279899

Reaction notes

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