Methyl iodide → HCID 66802638, compound

HRID 341417Notes

Reaction equation

HRID 341417 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:16]2[N:20]=[C:19]([C:21]3[C:22]([OH:27])=[N:23][CH:24]=[CH:25][CH:26]=3)[O:18][N:17]=2)[N:3]=1.[C:28](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:28][O:27][C:22]1[C:21]([C:19]2[O:18][N:17]=[C:16]([C:4]3[N:5]=[C:6]([N:8]([CH3:15])[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:7]=[C:2]([NH2:1])[N:3]=3)[N:20]=2)=[CH:26][CH:25]=[CH:24][N:23]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide3×HCID 11430Potassium CarbonateHCID 178482119HCID 178482119, compound2×

Product 1

HCID 66802638HCID 66802638, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-{3-[4-Amino-6-(methyl-phenyl-amino)-[1,3,5]triazin-2-yl]-[1,2,4]oxadiazol-5-yl}-pyridin-2-ol (Intermediate 63, 0.31 mmol) was added DMF (2 mL), potassium carbonate (85 mg, 0.52 mmol) and methyl iodide (19 μL, 0.31 mmol). The resulting mixture was stirred for 2 h, after which time further methyl iodide (40 μL, 0.62 mmol) was added. The reaction was stirred for a further 1.5 h after which time further methyl iodide (60 μL, 0.93 mmol) was added. This sequence was repeated two more times after which the starting material had been consumed. The crude mixture was diluted with ethyl acetate (10 mL), extracted with water (5 mL) and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the crude product was purified by chromatography on silica eluting with a gradient of 2% to 6% MeOH-DCM and then by trituration with hot methanol (2 mL) to give the title compound (44 mg, 38%)

Workup

  1. additionwas added
  2. customhad been consumed
  3. additionThe crude mixture was diluted with ethyl acetate (10 mL)
  4. extractionextracted with water (5 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationAfter concentration under reduced pressure
  7. customthe crude product was purified by chromatography on silica eluting with a gradient of 2% to 6% MeOH-DCM

Sources & evidence

ORD record
ord-35dd8902550e43ac9ea6f0d8569583d2
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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