Methyl iodide → HCID 11638343, compound

HRID 1668777Notes

Reaction equation

HRID 1668777 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([CH3:23])[N:14]=2)[CH3:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:24]I.[H-].[Na+]>CN(C=O)C>[CH3:23][C:15]1[N:14]=[C:13]([N:11]([C:8]2[CH:9]=[CH:10][C:5]([N:4]([CH3:24])[C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=2)[CH3:12])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11630903HCID 11630903, compound

Product 1

HCID 11638343HCID 11638343, compoundYield 600%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (4-acetamido-phenyl)-(2-methyl-quinazolin-4-yl)-methylamine (231 mg, 0.075 mmol) in 5 mL of DMF was added methyl iodide (0.9 g, 6.3 mmol) and the mixture was cooled to 0° C. Sodium hydride (60% oil suspension, 75 mg, 1.9 mmol) was added, and the mixture was stirred at 0° C. for 1 h, then allowed to warm to room temperature and stirred for 1 h. The reaction mixture was quenched by adding 50 uL of water, diluted with 25 mL of ethyl acetate, washed with water (25 mL×3) and saturated NaCl. The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by chromatography (90% ethyl acetate/hexanes) to give the title compound (143 mg, 0.45 mmol, 59%). 1H NMR (CDCl3): 7.19 (d, J=8.1, 1H), 7.54 (ddd, J=8.4, 6.6, 1.8, 1H), 7.16 (s, broad, 4H), 6.97-7.09 (m, 2H), 3.66 (s, 3H), 3.28 (s, 3H), 2.76 (s, 3H), 1.92 (s, 3H).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 1 h
  3. customThe reaction mixture was quenched
  4. additionby adding 50 uL of water
  5. additiondiluted with 25 mL of ethyl acetate
  6. washwashed with water (25 mL×3) and saturated NaCl
  7. dry with materialThe organic layer was dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography (90% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-41e8beb313ab45abb6df7db8709aae63
Source dataset
uspto-grants-2011_08
Patent number
US07989462B2

Reaction notes

Loading…