Methyl iodide → 1192559-21-9

HRID 1622041Notes

Reaction equation

HRID 1622041 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[C:4](=[O:25])[CH2:5][C:6]1[C:7]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([I:24])[CH:18]=2)=[N:8][N:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[N:11][C:10]=12)[CH3:2].[C:28]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[CH2:26]([N:3]([CH2:1][CH3:2])[C:4](=[O:25])[CH2:5][C:6]1[C:7]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:28])=[C:19]([I:24])[CH:18]=2)=[N:8][N:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[N:11][C:10]=12)[CH3:27]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 135995179HCID 135995179, compound

Product 1

HCID 584122261192559-21-9Yield 952.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4 (30 mg, 0.063 mmol) in DMF (5 mL) was added K2CO3 (300 mg, 2.2 mmol) and MeI (100 μL×2M, 0.2 mmol). The reaction was stirred overnight and the solvent was removed under vacuum and the residue was purified by silica gel column chromatography (EtOAc as eluent) to give 1 (29 mg, 0.60 mmol, 95%). 1H NMR (CD3OD, 400 MHz) δ 1.15 (t, J=7.2 Hz, 3H), 1.29 (t, J=7.2 Hz, 3H), 2.57 (s, 3H), 2.77 (s, 3H), 3.43 (q, J=7.2 Hz, 2H), 3.58 (q, J=7.2 Hz, 2H), 3.92 (s, 3H), 3.97 (s, 2H), 6.80 (s, 1H), 7.06 (d, J=8 Hz, 1H), 7.74 (d, J=8 Hz, 1H), 8.09 (s, 1H). ESI MS m/z: [M+H]+ C21H26IN4O2: calculated 493.1. found 493.1.

Workup

  1. customthe solvent was removed under vacuum
  2. customthe residue was purified by silica gel column chromatography (EtOAc as eluent)

Sources & evidence

ORD record
ord-94fd97f8caa54a3c9ad9bbbcea619da1
Source dataset
uspto-grants-2014_07
Patent number
US08778304B2

Reaction notes

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