Methyl iodide → HCID 59639574, compound

HRID 556586Notes

Reaction equation

HRID 556586 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:19]=[CH:18][C:17](=[O:20])[NH:16][C:10]=2[N:11]=[C:12]([S:14][CH3:15])[N:13]=1.[H-].[Na+].I[CH3:24]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH3:24])[C:10]=2[N:11]=[C:12]([S:14][CH3:15])[N:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59639533HCID 59639533, compound

Product 1

HCID 59639574HCID 59639574, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-fluoro-phenyl)-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (120 mg, 0.42 mmol) in 20 mL of anhyd THF was added NaH (50 mg, 1.2 mmol, 60% dispersion in mineral oil, 3 eq) followed by iodomethane (74 μL, 1.2 mmol, 3 eq). The reaction mixture was stirred 1 h at 23°, quenched with saturated aq NH4Cl. (20 mL), Et2O (100 mL) was added and the layers were separated. The organic layer was washed with satd aq NaCl, dried (MgSO4), filtered and evaporated. The yellow residue was then purified by Flash chromatography to afford 100 mg (92% yield) of 4-(2-Fluoro-phenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one. 1H-NMR δ 2.68 (s, 3H), 3.81 (s, 3H), 6.61 (d, 1H, J=9.8 Hz), 7.22 (m, 3H), 7.50 (m, 3H). LC MS (m/e)=302 (MH+). Rt=2.17 min.

Workup

  1. customquenched with saturated aq NH4Cl
  2. addition(20 mL), Et2O (100 mL) was added
  3. customthe layers were separated
  4. washThe organic layer was washed with satd aq NaCl
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe yellow residue was then purified by Flash chromatography

Sources & evidence

ORD record
ord-de1c2720fb454a92a1d2339e511bb0a8
Source dataset
uspto-grants-2011_11
Patent number
US08058282B2

Reaction notes

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