5-((5-chloropyridin-2-yl)(hydroxy)methyl)-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-6-(3-(trifluoromethoxy)phenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione → 3-(5-isopentyl-6-(2-isopropyl phenyl)-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propylformate
Reaction equation
ClC1C=C[C:5]([CH:8](O)[C:9]2[C:18]3[C:17](=[O:19])[N:16]([CH2:20][CH2:21][CH2:22][O:23][CH:24]4CCCC[O:25]4)[C:15](=[O:30])[N:14]([CH3:31])[C:13]=3[N:12]=[CH:11][C:10]=2[C:32]2[CH:37]=[CH:36][CH:35]=[C:34](OC(F)(F)F)[CH:33]=2)=NC=1>C(O)=O.CC(=O)OCC.O.[Zn]>[CH2:8]([C:9]1[C:18]2[C:17](=[O:19])[N:16]([CH2:20][CH2:21][CH2:22][O:23][CH:24]=[O:25])[C:15](=[O:30])[N:14]([CH3:31])[C:13]=2[N:12]=[CH:11][C:10]=1[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=1[CH:10]([CH3:32])[CH3:11])[CH2:5][CH:8]([CH3:9])[CH3:5]Participants
6
Reactant 1
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 5-((5-chloropyridin-2-yl)(hydroxy)methyl)-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-6-(3-(trifluoromethoxy)phenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (30 mg, 0.048 mmol) in HCOOH (1 mL) was added Zn dust (30 mg, 0.48 mmol). The reaction was heated at 80° C. for 30 min, cooled to RT then diluted with EA (2 mL) and water (2 mL). The organic layer was dried over Na2SO4 and concentrated to give 3-(5-isopentyl-6-(2-isopropyl phenyl)-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propylformate (30 mg, 90% yield) as a an oil. LCMS: MH+ 549 and TR=2.286 min. Used without further purification.
Workup
- temperaturecooled to RT
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-73b23402f70f48cfaeb346b2e1eed20c
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09440972B2
Reaction notes
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