Methyl iodide → Ammonium Hydroxide

HRID 1348898Notes

Reaction equation

HRID 1348898 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([CH2:15][O:16][CH:17]([C:26]3[N:30]([CH3:31])[CH:29]=[N:28][CH:27]=3)[C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)=[CH:10][NH:11][C:12](=[O:14])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].I[CH3:35]>CN(C=O)C.C(OCC)(=O)C>[NH4+:11].[OH-:14].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([CH2:15][O:16][CH:17]([C:26]3[N:30]([CH3:31])[CH:29]=[N:28][CH:27]=3)[C:18]3[CH:19]=[CH:20][C:21]([C:22]#[N:23])=[CH:24][CH:25]=3)=[CH:10][N:11]([CH3:35])[C:12](=[O:14])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10224657HCID 10224657, compound

Product 2

HCID 14923Ammonium HydroxideHCID 10182045HCID 10182045, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 44 (0.041 g, 0.1 mmol) in DMF (1.0 mL) at 0° C. was treated with 60% NaH in mineral oil (4 mg, 0.1 mmol), stirred for 15 minutes, treated with a 0° C. solution of iodomethane (15.6 mg, 0.11 mmol) in DMF (0.5 mL), stirred for 30 minutes, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10:1:0.1 EtOAc:MeOH:NH4OH to provide the desired product. MS (APCI) m/z 431 (M+H)+; 1H NMR(MeOH-d4) δ 8.92 (s, 1H), 8.19 (s, 1H), 7.73 (d, 2H), 7.50-7.41 (m, 5H), 7.32 (d, 1H), 7.24 (s, 1H), 6.67 (s, 1H), 5.86 (s, 1H), 4.52 (d, 1H), 4.40 (d, 1H), 3.79 (s, 3H), 3.67 (s, 3H).

Workup

  1. stirringstirred for 30 minutes
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 10:1:0.1 EtOAc

Sources & evidence

ORD record
ord-ca2ce424b2ef4b378298572e796144c5
Source dataset
uspto-grants-2007_05
Patent number
US07211595B2

Reaction notes

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