Water → HCID 57961782, compound

HRID 542057Notes

Reaction equation

HRID 542057 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([I:15])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([I:15])[CH:10]=2)[CH3:16])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57962262HCID 57962262, compound

Product 1

HCID 57961782HCID 57961782, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 2-chloro-N-(3-iodophenyl)pyrimidin-4-amine (1.1 g, 3.3 mmol) and potassium carbonate (0.92 g, 6.6 mmol) in N,N-dimethylformamide (6.6 mL) was treated with methyl iodide (0.52 mL, 8.3 mmol) and stirred at 20° C. for 5 h. The reaction mixture was poured into water (50 mL) and extracted with ethyl acetate (200 mL). The organic layer was separated and washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to a crude solid. This material was purified by flash column chromatography to give the desired product (0.87 g, 75%) as a tan oil. LCMS for C11H10ClIN3 (M+H)+: m/z=346.0.

Workup

  1. extractionextracted with ethyl acetate (200 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a crude solid
  7. customThis material was purified by flash column chromatography

Sources & evidence

ORD record
ord-7d584f6f63ba432d9177d35905e50975
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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