Dimethylformamide → 1-(2-aminopyrimidin-4-yl)-6-bromo-2,3-dihydro-1H-1,3-benzodiazol-2-one
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=1.CN([CH:20]=[O:21])C>>[NH2:16][C:12]1[N:11]=[C:10]([N:9]2[C:3]3[CH:4]=[C:5]([Br:8])[CH:6]=[CH:7][C:2]=3[NH:1][C:20]2=[O:21])[CH:15]=[CH:14][N:13]=1Participants
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 4-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine (400 mg, 1.43 mmol) in DMF (4 mL) was added N,N′-carbonyldiimidazole (255 mg, 1.57 mmol). The reaction was stirred at 80° C. overnight. Another portion of N,N′-carbonyldiimidazole (69 mg, 0.43 mmol) was added and heating was continued for another 2 hr at 80° C. The reaction mixture was concentrated in vacuo, diluted with water (10 mL) and extracted with ethyl acetate (2×20 mL). The organics were dried over Na2SO4, filtered and concentrated in vacuo. The resulting yellow solid was slurried in ethyl acetate and filtered off to give the title compound as a yellow solid: 1H (500 MHz, DMSO) δ 6.93 (2H, br. s.), 7.00 (1H, d, J=8.35 Hz), 7.31 (1H, d, J=10.25 Hz), 7.45 (1H, d, J=5.67 Hz), 8.25 (1H, d, J=5.52 Hz), 8.58 (1H, s); LC-MS: m/z=+306.0, 307.9 (M+H)+.
Workup
- temperatureheating
- waitwas continued for another 2 hr at 80° C
- concentrationThe reaction mixture was concentrated in vacuo
- additiondiluted with water (10 mL)
- extractionextracted with ethyl acetate (2×20 mL)
- dry with materialThe organics were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- filtrationfiltered off
Sources & evidence
- ORD record
- ord-c43a279c10ab441d888cdf56e9e24b66
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901313B2
Reaction notes
Loading…