Methyl iodide → HCID 10268360, compound

HRID 1270234Notes

Reaction equation

HRID 1270234 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([Cl:21])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]3[OH:14])[C:6]=2[N:7]=1.[H-].[Na+].[CH3:24]I>CN(C=O)C>[NH2:1][C:2]1[N:3]=[C:4]([Cl:21])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]3[O:14][CH3:24])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9944695HCID 9944695, compound

Product 1

HCID 10268360HCID 10268360, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a solution of the compound from Example 12, Step B (188 mg, 0.6 mmol) in anhydrous DMF (6 mL) was added NaH (60% in mineral oil; 26 mg, 0.66 mmol). The mixture was stirred at room temperature for 0.5 h and then cooled. MeI (45 μL) was added at 0° C. and the reaction mixture allowed to warm to 15° C. in 5 h. Then the mixture was poured into ice-water (20 mL) and extracted with CH2Cl2 (100+50 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL) and dried (Na2SO4). The evaporated residue was purified on a silica gel column with a solvent system of CH2Cl2/MeOH: 30/1. Appropriate fractions were pooled and evaporated to yield the title compound (50 mg) as a colorless glass.

Workup

  1. temperaturecooled
  2. temperatureto warm to 15° C. in 5 h
  3. extractionextracted with CH2Cl2 (100+50 mL)
  4. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. customThe evaporated residue was purified on a silica gel column with a solvent system of CH2Cl2/MeOH
  7. customevaporated

Sources & evidence

ORD record
ord-0306e97f22cb4e2c8b2d305ae4b1e711
Source dataset
uspto-grants-2007_04
Patent number
US07202224B2

Reaction notes

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