Pentylamine → HCID 12043766, compound

HRID 965661Notes

Reaction equation

HRID 965661 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH2:9][O:10][CH3:11])=[C:6]([CH3:12])[N:5]=[C:4]([NH2:13])[N:3]=1.[CH2:14]([NH2:19])[CH2:15][CH2:16][CH2:17][CH3:18]>O1CCOCC1>[NH2:13][C:4]1[N:3]=[C:2]([NH:19][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:7]([CH2:8][CH2:9][O:10][CH3:11])=[C:6]([CH3:12])[N:5]=1

Participants

4

Reactant 2

HCID 8060PentylamineHCID 22313247HCID 22313247, compound

Product 1

HCID 12043766HCID 12043766, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-chloro-5-(2-methoxyethyl)-6-methylpyrimidine-2-ylamine (150 mg, 0.74 mmol), amylamine (0.86 ml) and dioxane (1.5 ml) was kept at 90° C. for 7 hours. The reaction mixture was concentrated in vacuo, and the residue was extracted with chloroform and a saturated aqueous NaHCO3 solution. The organic layer was washed with saturated brine, dried over sodium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (4% MeOH:CHCl3) to give the object compound (108 mg, 57.5%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionthe residue was extracted with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified by column chromatography (4% MeOH:CHCl3)

Sources & evidence

ORD record
ord-e40108f2311d4b98b9c71a47d61eb0d3
Source dataset
uspto-grants-2005_10
Patent number
US06951866B2

Reaction notes

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