Guanidine Hydrochloride → ethyl 2-amino-4-(trifluoromethyl)pyrimidine-5-carboxylate
Reaction equation
[O-]CC.[Na+].Cl.[NH2:6][C:7]([NH2:9])=[NH:8].ClCCl.[CH2:13]([O:15][C:16](=[O:27])[C:17]([C:21](=O)[C:22]([F:25])([F:24])[F:23])=[CH:18]OC)[CH3:14]>C(O)C>[CH2:13]([O:15][C:16]([C:17]1[C:21]([C:22]([F:23])([F:24])[F:25])=[N:8][C:7]([NH2:9])=[N:6][CH:18]=1)=[O:27])[CH3:14]Participants
Procedure
Sodium ethoxide (2 eq, 83.8 mmol, 5.7 g) was added in one portion to a solution of guanidine hydrochloride (4 g, 41.9 mmol) in absolute ethanol (100 ml) and the resulting mixture was stirred at ambient temperature for 1 hour. A dichloromethane solution of 3-methoxy-2-(2,2,2-trifluoro-acetyl)-acrylic acid ethyl ester was then added and the mixture was stirred at ambient temperature for an additional 20 hours. The solvent was then removed by evaporation, water was added to the residue, and the mixture was stirred vigorously for 2 hours then allowed to stand at room temperature. The resulting solid was isolated by filtration, washed with water then dried in vacuo to afford 6.10 g (62% yield) of 2-amino-4-trifluoromethyl-pyrimidine-5-carboxylic acid ethyl ester. m/z (M+H)=236.2.
Workup
- stirringthe mixture was stirred at ambient temperature for an additional 20 hours
- customThe solvent was then removed by evaporation, water
- additionwas added to the residue
- stirringthe mixture was stirred vigorously for 2 hours
- customto stand at room temperature
- customThe resulting solid was isolated by filtration
- washwashed with water
- customthen dried in vacuo
Sources & evidence
- ORD record
- ord-4d486094f329406db59a7cb40a1ef281
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07563797B2
Reaction notes
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