Dichloromethane → 5-(4-Amino-3-bromo-phenyl)-1,3-dimethyl-tetrahydro-pyrimidin-2-one trifluoroacetic acid salt
Reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][N:18]([CH3:20])[C:17](=[O:21])[N:16]([CH3:22])[CH2:15]2)=[CH:10][CH:9]=1)(C)(C)C.C1C(=O)N([Br:31])C(=O)C1.C(Cl)Cl.C([O-])(O)=O.[Na+].[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41]>>[F:43][C:42]([F:45])([F:44])[C:40]([OH:46])=[O:41].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][N:18]([CH3:20])[C:17](=[O:21])[N:16]([CH3:22])[CH2:15]2)=[CH:10][C:9]=1[Br:31]Participants
Reactant 5
Product 1
Procedure
[4-(1,3-Dimethyl-2-oxo-hexahydro-pyrimidin-5-yl)-phenyl]-carbamic acid tert-butyl ester (as prepared in the previous step, 106 mg, 0.333 mmol) was dissolved in TFA (2 mL). The resulting mixture was stirred at RT for 30 min and concentrated. The residue obtained was dried in vacuo for 30 min and redissolved in DCM (5 mL). The resulting solution was cooled to 0° C. and NBS (64 mg, 0.35 mmol) was added. The reaction mixture was stirred at RT for 30 min and treated with DCM (20 mL) and satd aq NaHCO3 (20 mL). The organic layer was separated, dried (Na2SO4) and concentrated to afford the title compound (92 mg, 92%), which was directly used in next step without further purification. Mass spectrum (ESI, m/z): Calcd. for C12H16BrN3O, 298.0 and 300.0 (M+H). found 298.2 and 300.2.
Workup
- concentrationconcentrated
- customThe residue obtained
- customwas dried in vacuo for 30 min
- dissolutionredissolved in DCM (5 mL)
- temperatureThe resulting solution was cooled to 0° C.
- stirringThe reaction mixture was stirred at RT for 30 min
- customThe organic layer was separated
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-95b4d73b905348b38dd792dce8da0158
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296726B2
Reaction notes
Loading…