Methyl iodide → HCID 178490170, compound

HRID 81803Notes

Reaction equation

HRID 81803 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[C:7]([O:24][CH3:25])=[CH:8][C:9]([CH:21]([CH3:23])[CH3:22])=[C:10]([CH:20]=1)[O:11][C:12]1[CH:13]([NH2:19])[NH:14][C:15]([NH2:18])=[N:16][CH:17]=1.I[CH3:27].[OH-].[K+]>CC(C)=O>[CH:21]([C:9]1[CH:8]=[C:7]([O:24][CH3:25])[C:6]([C:2]2[N:1]([CH3:27])[CH:5]=[CH:4][N:3]=2)=[CH:20][C:10]=1[O:11][C:12]1[CH:13]([NH2:19])[NH:14][C:15]([NH2:18])=[N:16][CH:17]=1)([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178490171HCID 178490171, compound

Product 1

HCID 178490170HCID 178490170, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 5-[5-(1H-Imidazol-2-yl)-2-isopropyl-4-methoxy-phenoxy]-3,4-dihydro-pyrimidine-2,4-diamine (0.044 g, 0.129 mmols) and iodomethane (9 ul, 0.145 mmols) in acetone (5 ml) was added KOH (0.055 g, 0.98 mmols), the mixture was heated at 30° C. for 20 minutes, the mixture was filtered through celite, washed with CH2Cl2, the combined organic solution was concentrated in vacuo. The residue was purified via preparative TLC silica plates, eluted with 5% MeOH/CH2Cl2/NH4OH four times to give 5-[2-Isopropyl-4-methoxy-5-(1-methyl-1H-imidazol-2-yl)-phenoxy]-3,4-dihydro-pyrimidine-2,4-diamine (0.024 g, 52%). Mass Spec: M+H: 355.

Workup

  1. filtrationthe mixture was filtered through celite
  2. washwashed with CH2Cl2
  3. concentrationthe combined organic solution was concentrated in vacuo
  4. customThe residue was purified via preparative TLC silica plates
  5. washeluted with 5% MeOH/CH2Cl2/NH4OH four times

Sources & evidence

ORD record
ord-6e4bd59f8b2145fbaed2e5cd033e96a2
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

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