Sodium Methoxide → HCID 24794431, compound
Reaction equation
Cl.Cl.[C:3](=[NH:9])([NH2:8])[CH2:4][C:5](=[NH:7])[NH2:6].C[O-].[Na+].[F:13][C:14]1[CH:34]=[CH:33][CH:32]=[CH:31][C:15]=1[CH2:16][C:17]1[N:18]=[C:19]([C:26](OCC)=O)[N:20]2[CH:25]=[CH:24][CH:23]=[N:22][C:21]=12>CO>[F:13][C:14]1[CH:34]=[CH:33][CH:32]=[CH:31][C:15]=1[CH2:16][C:17]1[N:18]=[C:19]([C:26]2[N:9]=[C:3]([NH2:8])[CH:4]=[C:5]([NH2:6])[N:7]=2)[N:20]2[CH:25]=[CH:24][CH:23]=[N:22][C:21]=12Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
147 mg (0.85 mmol) of 1,3-propanediimidamide dihydrochloride are introduced into 2 ml of methanol, and 0.37 ml (2.00 mmol) of a 30% strength methanolic sodium methanolate solution is added. The mixture is heated at 50° C. for 30 min. It is then allowed to cool to RT, a solution of 150 mg (0.50 mmol) of ethyl 8-(2-fluorobenzyl)imidazo[1,5-a]pyrimidine-6-carboxylate from example 10A in 2.0 ml of methanol is added, and the mixture is heated to reflux for 3 h. Cooling is followed by dilution with water and extraction with ethyl acetate. The organic phase is dried over sodium sulfate, and the solvent is removed in vacuo. The residue is purified by preparative HPLC to result in 36 mg (21% of theory) of the desired product as yellow crystals.
Workup
- additionis added
- temperatureto cool to RT
- temperaturethe mixture is heated
- temperatureto reflux for 3 h
- temperatureCooling
- extractionis followed by dilution with water and extraction with ethyl acetate
- dry with materialThe organic phase is dried over sodium sulfate
- customthe solvent is removed in vacuo
- customThe residue is purified by preparative HPLC
Sources & evidence
- ORD record
- ord-1b0ad55e63ad40f29f0d50c19895cbe2
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08309551B2
Reaction notes
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