Water → HCID 57962415, compound

HRID 541921Notes

Reaction equation

HRID 541921 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[CH:10]=2)[C:5]([Cl:22])=[CH:4][N:3]=1.[C:23](=O)([O-])[O-].[K+].[K+].CI.O>C(#N)C>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:23])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[CH:10]=2)[C:5]([Cl:22])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 57962046HCID 57962046, compound

Product 1

HCID 57962415HCID 57962415, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 2,5-dichloro-N-[3-(tetrahydro-2H-pyran-2-yloxy)phenyl]pyrimidin-4-amine (110 mg, 0.32 mmol) in acetonitrile (3 mL) was treated with potassium carbonate (89 mg, 0.65 mmol) followed by methyl iodide (60 μL, 0.97 mmol) and heated at 70° C. for 16 h. The reaction mixture was treated with additional methyl iodide (60 μL, 0.97 mmol) and heated at 70° C. for 11 h. The reaction mixture was cooled to 25° C., poured into water (30 mL), and extracted with ethyl acetate (50 mL). The organic layer was separated and washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to give a crude oil. This material was purified by flash column chromatography to give the desired product (68 mg, 59%) as a clear oil. LCMS for C16H18Cl2N3O2 (M+H)+: m/z=354.0, 356.0.

Workup

  1. temperatureheated at 70° C. for 11 h
  2. temperatureThe reaction mixture was cooled to 25° C.
  3. extractionextracted with ethyl acetate (50 mL)
  4. customThe organic layer was separated
  5. washwashed with brine (20 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto give a crude oil
  10. customThis material was purified by flash column chromatography

Sources & evidence

ORD record
ord-dc872f5b497346b2a3ca9007806d532d
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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