Methyl iodide → HCID 86710525, compound

HRID 341501Notes

Reaction equation

HRID 341501 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]([F:15])=[CH:13][CH:14]=2)[N:5]=[C:4]([NH2:16])[N:3]=1.[H-].[Na+].IC.[CH3:21]COC(C)=O>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([C:9]2[CH:10]=[N:11][C:12]([F:15])=[CH:13][CH:14]=2)[CH3:21])[N:5]=[C:4]([NH2:16])[N:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 86710526HCID 86710526, compound2×

Product 1

HCID 86710525HCID 86710525, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-chloro-2-N-(6-fluoropyridin-3-yl)-1,3,5-triazine-2,4-diamine (Intermediate 159, 0.52 g, 2.17 mmol) in DMF (1 mL) at 0 C under nitrogen was added portionwise sodium hydride (60% dispersion in mineral oil, 0.0869 g, 2.17 mmol). The mixture was stirred for 5 min, then iodomethane (0.3 g, 2.17 mmol) was added and the mixture was heated to 50 C for 16 h. EtOAc was added and the organic layer was washed with saturated aq. sodium bicarbonate, dried over sodium sulfate and concentrated. The residue was purified by FCC, eluting with 10-50% EtOAc in heptane to afford the title compound (0.089 g, 16% yield). Method B HPLC-MS: MH+ requires m/z=255 Found: m/z=255, Rt=1.52 min (74%).

Workup

  1. temperaturethe mixture was heated to 50 C for 16 h
  2. washthe organic layer was washed with saturated aq. sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by FCC
  6. washeluting with 10-50% EtOAc in heptane

Sources & evidence

ORD record
ord-1ef14166c1cf481bb30810f67a1af2fa
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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