Acetonitrile → 2-Cyano-5-pyrimidinylcarbamoyl-beta-alanine
Reaction equation
C([C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[CH:5][N:4]=1)#N.[N-:10]=[C:11]=[O:12].C([O:15][C:16](=[O:20])[CH2:17][CH2:18][NH2:19])C.[OH-].[Na+].[C:23](#N)C>>[C:18]([CH:17]([C:16]([OH:15])=[O:20])[CH2:23][NH:10][C:11](=[O:12])[NH:9][C:6]1[CH:7]=[N:8][CH:3]=[N:4][CH:5]=1)#[N:19]Participants
Procedure
A solution of 0.83 g (7 mmol) of 2-cyano-5aminopyrimidine and 1 g (7 mmol) of beta-alanine ethyl ester isocyanate in 30 ml of anhydrous acetonitrile is heated for 4 hr at 70° C. The reaction mixture is concentrated to dryness and the residue is subjected directly to hydrolysis with 0.1 N HCl (50 ml) for 3 hr at 70° C. After cooling, the solution is treated with NaOH until a pH of 10 is obtained, washed with 3 × 40 ml of dichloromethane, acidified with HCl until a pH of 3 is obtained, and then concentrated to dryness in vacuum. The residue is treated with absolute ethanol whichpermits, by concentration of the ethanolic extract to dryness, 0.74 g (yield 45%) of 2-cyano-5-pyrimidinylcarbamoyl-beta-alanine to be obtained in the form of a solid having a melting point of 183° C.
Workup
- concentrationThe reaction mixture is concentrated to dryness
- customthe residue is subjected directly to hydrolysis with 0.1 N HCl (50 ml) for 3 hr at 70° C
- temperatureAfter cooling
- customis obtained
- washwashed with 3 × 40 ml of dichloromethane
- customis obtained
- concentrationconcentrated to dryness in vacuum
- additionThe residue is treated with absolute ethanol whichpermits, by concentration of the
Sources & evidence
- ORD record
- ord-d0de3dc69dce4556bd4075a0da9d74bf
- Source dataset
- uspto-grants-1991_03
- Patent number
- US04997667
Reaction notes
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