Bromoform → 4-bromo-2-[[(2,3-difluorophenyl)methyl]thio]-7(8H)-pteridinone
Reaction equation
N[C:2]1[C:11]2[N:10]=[CH:9][C:8](=[O:12])[NH:7][C:6]=2[N:5]=[C:4]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=2[F:22])[N:3]=1.C(Br)(Br)[Br:24].C(ON=O)CC(C)C.C(#N)C>CS(C)=O.CCOCC>[Br:24][C:2]1[C:11]2[N:10]=[CH:9][C:8](=[O:12])[NH:7][C:6]=2[N:5]=[C:4]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=2[F:22])[N:3]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
The product of step (d) (6.0 g) was suspended in DMSO (90 ml) and bromoform (60 ml) was added and the mixture was heated to 100° C. Isopentylnitrite (25 ml) was added and the mixture stirred for 5 min. The mixture was quickly cooled in an ice bath then evaporated to leave an oil. This was repeated three times. Acetonitrile (200 ml) was added and the solid which separated was removed by filtration. The solvent was evaporated and the residue was purified by flash chromatography, eluting with dichloromethane and then 5% ethyl acetate in dichloromethane to give a yellow solid which was slurried with ether then collected. The solid was washed with ether and dried to give the subtitled compound as a colourless solid (8.74 g).
Workup
- temperatureThe mixture was quickly cooled in an ice bath
- customthen evaporated
- customto leave an oil
- customthe solid which separated
- customwas removed by filtration
- customThe solvent was evaporated
- customthe residue was purified by flash chromatography
- washeluting with dichloromethane
- custom5% ethyl acetate in dichloromethane to give a yellow solid which
- customthen collected
- washThe solid was washed with ether
- customdried
Sources & evidence
- ORD record
- ord-5402c5ba4f0f4a4094446435dc218c4f
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07579342B2
Reaction notes
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