Diisopropylethylamine → (R)-7-chloro-3-methyl-5-(tetrahydrofuran-3-ylamino)pyrido[4,3-d]pyrimidin-4(3H)-one
Reaction equation
Cl[C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH3:13])[CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([Cl:14])[N:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:26][C@@H:27]1[CH2:31][CH2:30][O:29][CH2:28]1.CCN(C(C)C)C(C)C>O1CCOCC1>[Cl:14][C:4]1[N:3]=[C:2]([NH:26][C@@H:27]2[CH2:31][CH2:30][O:29][CH2:28]2)[C:11]2[C:10](=[O:12])[N:9]([CH3:13])[CH:8]=[N:7][C:6]=2[CH:5]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 5,7-dichloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (75 mg, 0.33 mmol), (R)-3-aminotetrahydrofuran toluene-4-sulfonate (101 mg, 0.39 mmol), Hunig's base (0.23 mL, 1.32 mmol) and dioxane (4 mL) was stirred at 90° C. overnight. The reaction mixture was cooled to room temperature and worked-up. The residue was purified using slilica gel flash column chromatography (eluent: 0-10% methanol in dichloromethane) to afford (R)-7-chloro-3-methyl-5-(tetrahydrofuran-3-ylamino)pyrido[4,3-d]pyrimidin-4(3H)-one as a white solid.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- customThe residue was purified
Sources & evidence
- ORD record
- ord-4f5b6b8d5c7645a4843bb97d9fcc2449
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722692B2
Reaction notes
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