HCID 54757315, compound → HCID 135979570, compound
Reaction equation
[CH3:1][C:2]1[C:6]([C:7]([NH2:9])=[O:8])=[C:5]([NH:10][C:11](=O)[CH2:12][CH:13]([CH3:15])[CH3:14])[S:4][N:3]=1>N>[CH2:12]([C:11]1[NH:9][C:7](=[O:8])[C:6]2[C:2]([CH3:1])=[N:3][S:4][C:5]=2[N:10]=1)[CH:13]([CH3:15])[CH3:14]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
3-Methyl-5-(3-methyl-butyrylamino)-isothiazole-4-carboxylic acid amide (method 25) (6 g, 25 mmol) was suspended in 150 mL of 30% NH3 and then was heated to 140° C. for 5 h in a pressure reactor. The mixture was cooled and neutralized to pH 7. The reaction mixture was extracted with EtOAc (3×100 mL) and the combined organic layers were washed with water (100 mL), brine (100 mL) and concentrated to get the crude product which was further purified by column (silica gel) chromatography using 30% EtOAc in hexanes as eluent. Concentration of the pure product fractions provided 6-isobutyl-3-methyl-5H-isothiazolo[5,4-d]pyrimidin-4-one (2.2 g, 38%) as an off-white powder. 1H NMR (300 MHz) δ 1.05 (d, 6H), 2.32 (m, 1H), 2.69 (d, 2H), 2.82 (s, 3H).
Workup
- temperatureThe mixture was cooled
- extractionThe reaction mixture was extracted with EtOAc (3×100 mL)
- washthe combined organic layers were washed with water (100 mL), brine (100 mL)
- concentrationconcentrated
- customto get the crude product which
- customwas further purified by column (silica gel) chromatography
Sources & evidence
- ORD record
- ord-415a6ebd4492432b8814bf1a6a72c014
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07498333B2
Reaction notes
Loading…