7-chloro-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one → 2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one
Reaction equation
Cl[C:2]1[NH:7][C:6](=[O:8])[N:5]2[CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:4]2[CH:3]=1>CCOC(C)=O.CO.[OH-].[Pd+2].[OH-]>[O:13]([CH2:12][C:10]1[N:11]=[C:4]2[CH:3]=[CH:2][NH:7][C:6](=[O:8])[N:5]2[CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Participants
Procedure
10% Palladium hydroxide (0.43 g, 3 mmol) was added to a solution of 7-chloro-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (0.24 g, 0.85 mmol) and TEA (0.6 mL, 4.32 mmol) in a mixture of AcOEt and MeOH (60 mL). The mixture was hydrogenated in a Parr reactor (45 psi) at 50° C. for 16 hours. Then 10% palladium hydroxide (0.18 g, 0.43 mmol) was added and the mixture hydrogenated again in a Parr reactor (45 psi) at 50° C. for 16 hours. The mixture was hydrogenated over 5 cycles with addition of 10% palladium hydroxide (0.18 g, 0.43 mmol) every cycle. The mixture was filtered through a pad of diatomaceous earth and washed with MeOH. The solvents were evaporated in vacuo and the crude product purified by flash column chromatography (silica; 7 M solution of ammonia in MeOH in DCM with a gradient of 0/100 to 40/60). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (0.19 g, 92% yield) as a white solid.
Workup
- waitthe mixture hydrogenated again in a Parr reactor (45 psi) at 50° C. for 16 hours
- filtrationThe mixture was filtered through a pad of diatomaceous earth
- washwashed with MeOH
- customThe solvents were evaporated in vacuo
- customthe crude product purified by flash column chromatography (silica
- customThe desired fractions were collected
- customthe solvents evaporated in vacuo
Sources & evidence
- ORD record
- ord-6821acc5ca40471cac39aef63718834c
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865725B2
Reaction notes
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