Hydrochloric Acid → 4-methyl-2-(2-thiazolyl)-5-Pyrimidinecarboxylic acid
Reaction equation
[C:1]([C:3]1[S:4][CH:5]=[CH:6][N:7]=1)#[N:2].C(N[C@H](C(O)=O)CS)(=O)C.C([O-])(=O)C.[NH4+].C([O:25][C:26](=[O:35])[C:27](=[CH:31][N:32](C)C)[C:28](=O)[CH3:29])C.CC([O-])(C)C.[K+].[OH-].[K+].Cl>CO.O>[CH3:29][C:28]1[C:27]([C:26]([OH:35])=[O:25])=[CH:31][N:32]=[C:1]([C:3]2[S:4][CH:5]=[CH:6][N:7]=2)[N:2]=1Participants
Reactant 7
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
A solution of 2-cyanothiazole (1.55 g, 14.2 mmol) in MeOH (12 mL) is treated with N-acetylcysteine (234 mg, 1.42 mmol), ammonium acetate (1.5 g, 18.5 mmol) and heated in a microwave at 120° C. for 15 min. The mixture is then treated with 2-dimethylaminomethylene-3-oxo-butyric acid ethyl ester (3.2 g, 17.0 mmol) and KOt-Bu (2.2 g, 20 mmol), and heated in a microwave at 120° C. for an additional 15 min. The mixture is then treated with a solution of KOH (1.2 g, 20 mmol) in H2O (5 mL) and heated at reflux for 1 h. The mixture is neutralized with concentrated aqueous HCl. The precipitate is collected by filtration and dried to afford 4-methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (1.95 g, 62%). MS: 222 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 13.77 (s. OH, 1H), 9.18 (s, 1H), 8.13 (d, 1H), 8.07 (d, 1H), 2.81 (s, 3H).
Workup
- temperatureheated in a microwave at 120° C. for an additional 15 min
- temperatureheated
- temperatureat reflux for 1 h
- filtrationThe precipitate is collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-f076bc0c8c6e41929ee30c1538018483
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258130B2
Reaction notes
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