Water → HCID 86660229, compound

HRID 2042714Notes

Reaction equation

HRID 2042714 reaction equation
[Br:1][C:2]1[C:7]([NH2:8])=[CH:6][N:5]=[CH:4][N:3]=1.CC(C)([O-])C.[Na+].I[CH2:16][CH2:17][CH2:18][CH3:19].O>CC(N(C)C)=O>[Br:1][C:2]1[C:7]([NH:8][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:6][N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10962Butyl iodideHCID 23676156Sodium t-butoxideHCID 457897744-Bromopyrimidin-5-amine

Product 1

HCID 86660229HCID 86660229, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-bromopyrimidin-5-amine (1 g, 5.75 mmol), sodium tert-butoxide (1.11 g, 11.5 mmol) and 1-iodobutane (1.11 g, 6.03 mmol) in DMA (15 mL) was heated at 60° C. for 15 hours. The mixture was poured into water 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 (hexanes-EtOAc 3:1) to afford 300 mg of the title compound. MS (ESI) m/z 230 (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 (hexanes-EtOAc 3:1)

Sources & evidence

ORD record
ord-509645f6c45b4840ad0ef5bbfb32b402
Source dataset
uspto-grants-2013_11
Patent number
US08586596B2

Reaction notes

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