Hydrochloric Acid → 5-(2-Fluoro-4-iodophenylamino)-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione
Reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:17](=[O:19])[NH:16][CH:15]=[N:14][C:13]=3[N:12]([CH3:20])[C:11](=[O:21])[C:10]=2[CH3:22])=[C:4]([F:23])[CH:3]=1.Cl.N([O-])=O.[Na+].[I-:29].[K+]>C(O)(=O)C.O.II>[F:23][C:4]1[CH:3]=[C:2]([I:29])[CH:7]=[CH:6][C:5]=1[NH:8][C:9]1[C:18]2[C:17](=[O:19])[NH:16][CH:15]=[N:14][C:13]=2[N:12]([CH3:20])[C:11](=[O:21])[C:10]=1[CH3:22]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
The title compound was synthesized from compound 9E (1.74 g, 5.5 mmol) which was first dissolved in a 1:1 mixture of acetic acid and water (10 mL) at 0° C. Concentrated HCl (1.2 mL) in water (2 mL) was slowly added and the mixture stirred for 20 minutes. Sodium nitrite (381 mg, 5.5 mmol, 1 eq) in water (800 μL) was added and the solution stirred for 20 minutes. Potassium iodide (4.58 g, 27.6 mmol, 5 eq) and iodine (20 mg, cat) was added and the reaction allowed to RT then stirred for 1 hour at 90° C. After cooling, the mixture was evaporated in vacuo. The residue was purified by silica chromatography eluting with 10% methanol in DCM to give 1.21 g of the title compound (51%). [M+H] calc'd for C15H12FIN4O2, 427. found, 427.
Workup
- stirringthe solution stirred for 20 minutes
- customallowed to RT
- stirringthen stirred for 1 hour at 90° C
- temperatureAfter cooling
- customthe mixture was evaporated in vacuo
- customThe residue was purified by silica chromatography
- washeluting with 10% methanol in DCM
Sources & evidence
- ORD record
- ord-7911dc5da3c04555972a5fb4503faec4
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08470837B2
Reaction notes
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