Sodium Hydroxide → 6-(5-chloro-6-methoxy-3-pyridinyl)-1,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-one
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:21][CH2:20][C:13]3[N:14]=[CH:15][N:16]=[C:17]([O:18]C)[C:12]=3[CH2:11]2)[CH:5]=[N:6][C:7]=1[O:8][CH3:9].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:21][CH2:20][C:13]3[N:14]=[CH:15][N:16]=[C:17]([OH:18])[C:12]=3[CH2:11]2)[CH:5]=[N:6][C:7]=1[O:8][CH3:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To 6-(5-chloro-6-methoxy-pyridin-3-yl)-4-methoxy-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine (intermediate 15)(95 mg, 0.31 mmol) in MeOH (5.0 mL) in a glass vial was added 2M NaOH(aq) (3.0 mL). The vial was capped and heated at 90° C. for 24 h. Acidified with glacial AcOH to pH 6, evaporated in vacuo and the residue extracted with CH2Cl2 (1×50 mL with stirring). With each extraction, the CH2Cl2 layer was decanted from the solid residue. The CH2Cl2 layers were combined. The solid residue was then washed with water (10 mL) and filtered. This filtered solid was combined with the CH2Cl2 layers and evaporated in vacuo to give 6-(5-chloro-6-methoxy-pyridin-3-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-ol as a yellow solid (90 mg, 107% yield) LCMS: [M+H]+=293.0/294.8, Rt(3)=1.38 min.
Workup
- customThe vial was capped
- customAcidified with glacial AcOH to pH 6, evaporated in vacuo
- extractionthe residue extracted with CH2Cl2 (1×50 mL with stirring)
- extractionWith each extraction
- customthe CH2Cl2 layer was decanted from the solid residue
- washThe solid residue was then washed with water (10 mL)
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-0adb5dbcfc28475485aad3147fdc7aa6
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653092B2
Reaction notes
Loading…