Butyl iodide → HCID 86660228, compound

HRID 2042712Notes

Reaction equation

HRID 2042712 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH3:10][C:11]([CH3:14])([O-:13])[CH3:12].[Na+].I[CH2:17][CH2:18][CH2:19][CH3:20].C([O-])(O)=O.[Na+]>CC(N(C)C)=O.O>[C:11]([O:13][C:6]1[C:7]([NH:8][CH2:17][CH2:18][CH2:19][CH3:20])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1)([CH3:14])([CH3:12])[CH3:10]

Participants

7

Reactant 4

HCID 10962Butyl iodideHCID 794345-Amino-4,6-dichloropyrimidineHCID 516892Sodium BicarbonateHCID 23676156Sodium t-butoxide

Product 1

HCID 86660228HCID 86660228, compoundYield 7.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4,6-dichloropyrimidin-5-amine (1.64 g, 10 mmol), sodium tert-butoxide (1.92 g, 20 mmol) and 1-iodobutane (2.02 g, 11 mmol) in DMA (30 mL) was heated at 50° C. for 12 hours. The mixture was poured into water, treated with saturated aqueous NaHCO3 and extracted with ethyl acetate. The acetate layer was washed with water, brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography (hexane-EtOAc 1:1) to afford 200 mg of the title compound. MS (ESI) m/z 258 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe acetate layer was washed with water, brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography (hexane-EtOAc 1:1)

Sources & evidence

ORD record
ord-abe216a5100448c08f5d9560a080433b
Source dataset
uspto-grants-2013_11
Patent number
US08586596B2

Reaction notes

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