Methanol → 5,7-dichloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1805756Notes

Reaction equation

HRID 1805756 reaction equation
[Cl:1][C:2]1[C:11]2[C:10](=[O:12])[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([Cl:13])[N:3]=1.[H-].[Na+].[CH3:16]I.CO>CN(C=O)C>[Cl:1][C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH3:16])[CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([Cl:13])[N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1357415885,7-Dichloropyrido[4,3-d]pyrimidin-4(3H)-one

Product 1

HCID 580929485,7-dichloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5,7-dichloropyrido[4,3-d]pyrimidin-4(3H)-one (1 g, 4.65 mmol) was dissolved in anhydrous DMF 15 mL, and NaH (60% mineral oil, 205 mg, 5.11 mmol) was slowly added into the reaction solution. The reaction was stirred at room temperature for 15 minutes, then CH3I (730 mg, 5.11 mmol) in DMF was added drop-wise into the solution. The reaction was heated to 50° C. for 1 hour and then cooled down to room temperature. Methanol was then added to quench the reaction and the solvent was removed under the vacuum. The crude product was purified by silica column chromatography using hexane/ethyl acetate 1:1 to obtain the final compound 5,7-dichloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one. 1H NMR (DMSO-d6) δ 8.64 (s, 1H), 7.74 (s, 1H), 3.46 (s, 3H); ESI-MS m/z 230.1 (MH+).

Workup

  1. temperatureThe reaction was heated to 50° C. for 1 hour
  2. temperaturecooled down to room temperature
  3. customto quench
  4. customthe reaction
  5. customthe solvent was removed under the vacuum
  6. customThe crude product was purified by silica column chromatography

Sources & evidence

ORD record
ord-5b3854bde5bb4e7da7e6f70ec158c9b5
Source dataset
uspto-grants-2013_01
Patent number
US08354526B2

Reaction notes

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