Methyl iodide → HCID 18381619, compound

HRID 2297458Notes

Reaction equation

HRID 2297458 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:25])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[C:12]([NH:21][CH2:22]CC)=[N:11][N:10]=1.[C:26]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:25])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[C:12]([N:21]([CH3:26])[CH3:22])=[N:11][N:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18381597HCID 18381597, compound

Product 1

HCID 18381619HCID 18381619, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

At room temperature a solution of [4-(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-phthalazin-1-yl]-propyl-amine (3.5 g, 5.64 mmoles), prepared as described in example 78, in DMF (35 ml) was stirred under N2, then added with K2CO3 (0.78 g, 5.64 mmoles) and methyl iodide (0.35 ml, 5.64 mmoles). The mixture was heated at 50° C. and after 20 hours was dried and partitioned between water and CH2Cl2. The organic phase was washed with water, anhydrified and concentrated to give an oil which was flash chromatographed (eluent: hexane/ethyl acetate 4:6) to give 1 g of the title compound (yield: 50%). m.p.: 170-173° C.

Workup

  1. customwas dried
  2. custompartitioned between water and CH2Cl2
  3. washThe organic phase was washed with water, anhydrified
  4. concentrationconcentrated
  5. customto give an oil which
  6. customchromatographed (eluent: hexane/ethyl acetate 4:6)

Sources & evidence

ORD record
ord-6ad7cd2f685342b7a4bfb69adc9bc271
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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