Dimethylbarbituric acid → 2-amino-N-(3,5-difluoro-4-(trimethylsilyl)phenyl)-2-(4-(methoxymethyl)phenyl) acetamide
Reaction equation
C([N:4](CC=C)[CH:5]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][O:28][CH3:29])=[CH:23][CH:22]=1)[C:6]([NH:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([Si:16]([CH3:19])([CH3:18])[CH3:17])=[C:11]([F:20])[CH:10]=1)=[O:7])C=C.CN1C(=O)CC(=O)N(C)C1=O>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:4][CH:5]([C:21]1[CH:22]=[CH:23][C:24]([CH2:27][O:28][CH3:29])=[CH:25][CH:26]=1)[C:6]([NH:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([Si:16]([CH3:17])([CH3:18])[CH3:19])=[C:11]([F:20])[CH:10]=1)=[O:7]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 2-(diallylamino)-N-(3,5-difluoro-4-(trimethylsilyl)phenyl)-2-(4-(methoxymethyl)phenyl)acetamide (6.79 g, 14.81 mmol) and 1,3-dimethylbarbituric acid (4.85 g, 31.09 mmol) in THF (120 mL) was added Pd(PPh3)4 (0.684 g, 0.59 mmol), and the mixture was stirred overnight at room temperature under argon atmosphere. The reaction solution was concentrated, and the obtained residue was purified by silica gel column chromatography (NH, solvent gradient; 50→100% ethyl acetate/hexane) to give crude 2-amino-N-(3,5-difluoro-4-(trimethylsilyl)phenyl)-2-(4-(methoxymethyl)phenyl)acetamide (4.00 g) as a colorless oil.
Workup
- concentrationThe reaction solution was concentrated
- customthe obtained residue was purified by silica gel column chromatography (NH, solvent gradient; 50→100% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-18fbb32b88064cc886a06925a3f454de
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365520B2
Reaction notes
Loading…