Ethyl bromoacetate → HCID 90303921, compound
Reaction equation
Cl[C:2]1[CH:11]=[C:6]2[NH:7][CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:12])[N:3]=1.[H-].[Na+].Br[CH2:16][C:17]([O:19]CC)=[O:18].[F:22][C:23]1[CH:24]=[C:25]([CH2:30][OH:31])[CH:26]=[CH:27][C:28]=1[F:29]>O1CCCC1>[F:22][C:23]1[CH:24]=[C:25]([CH:26]=[CH:27][C:28]=1[F:29])[CH2:30][O:31][C:2]1[CH:11]=[C:6]2[N:7]([CH2:16][C:17]([OH:19])=[O:18])[CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:12])[N:3]=1Participants
6
Procedure
To a solution of 8-chloro-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (5 g, 26.9 mmol) in tetrahydrofuran (20 mL) was added sodium hydride (2.59 g, 108 mmol) at r.t. stirred for 10 minutes at r.t., then was added ethyl 2-bromoacetate (4.50 g, 26.9 mmol) and stirred for 2 h, and followed by addition of (3,4-difluoro phenyl)methanol (3.88 g, 26.9 mmol). The reaction mixture was stirred for 1 h at r.t., quenched by addition of water, and extracted by EtOAc. The aqueous phase was acidified to pH˜1 with HCl (1N), washed by EtOAc, then the aqueous phase was concentrated in vacuum, and the residual was washed by methanol and filtrated. The filtrate was concentrated to afford the title compound (3.1 g)
Workup
- stirringstirred for 2 h
- stirringThe reaction mixture was stirred for 1 h at r.t.
- customquenched by addition of water
- extractionextracted by EtOAc
- washwashed by EtOAc
- concentrationthe aqueous phase was concentrated in vacuum
- washthe residual was washed by methanol
- filtrationfiltrated
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-3300dc6f5b964b05ab7ea71dd6f1a9a9
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296755B2
Reaction notes
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