Sodium ethoxide → HCID 178433412, compound
Reaction equation
N[C:2]1[NH:3][C:4](=O)[C:5]2CC(C)[CH2:8][C:6]=2[N:7]=1.[O-:13][CH2:14][CH3:15].[Na+].C(C(CC(OCC)OCC)C(OCC)=O)#[N:18]>>[CH3:8][C:6]1[NH:7][C:2]2=[N:3][CH:4]=[CH:5][C:15]2=[C:14]([OH:13])[N:18]=1Participants
Procedure
Acetamidine hydrochloride (2, 0.05 mol, 4.7 g) was added to the 0.1 M sodium ethoxide solution (75 ml) and kept stirring under room temperature for 0.5 h. After removing the formed sodium chloride by filtration, the filtrate was added the ethyl α-cyano-γ,γ-diethoxybutyrate (1, 0.05 mol, 11.5 g) and the solution was heated under reflux for 5 h. After the removal of most solvent under vacuum, acetic acid was added to adjust the pH to 7.0 and 10.8 g precipitation as white powder. Ethanol (110 ml) with concentrated sulfuric acid (2 ml) was added to the collected powder and was refluxed for 2 h. By the end of the reaction an equal volume of water was added and kept at 4° C. overnight. The pyrrolopyrimidine 3 precipitated as white powder (2.1 g) was used for next step without further purification.
Workup
- customAfter removing the formed sodium chloride
- filtrationby filtration
- temperaturethe solution was heated
- temperatureunder reflux for 5 h
- customAfter the removal of most solvent under vacuum, acetic acid
- additionwas added
- customto 7.0 and 10.8 g precipitation as white powder
- additionEthanol (110 ml) with concentrated sulfuric acid (2 ml) was added to the collected powder
- temperaturewas refluxed for 2 h
- customBy the end of the reaction an equal volume of water
- additionwas added
- waitkept at 4° C. overnight
- customThe pyrrolopyrimidine 3 precipitated as white powder (2.1 g)
- customwas used for next step without further purification
Sources & evidence
- ORD record
- ord-dbd8c47c1d3a48f495ece361b8b3e857
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946239B2
Reaction notes
Loading…