Pentylamine → N-(2-Amino-5-benzyl-6-methylpyrimidine-4-yl)-N-pentylamine

HRID 965664

Reaction equation

HRID 965664 reaction equation
[CH2:1]([C:8]1[C:9](Cl)=[N:10][C:11]([NH2:15])=[N:12][C:13]=1[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([NH2:22])[CH2:18][CH2:19][CH2:20][CH3:21]>O1CCOCC1>[NH2:15][C:11]1[N:10]=[C:9]([NH:22][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:13]([CH3:14])[N:12]=1

Participants

4

Reactant 2

HCID 8060PentylamineHCID 8202385-Benzyl-4-chloro-6-methylpyrimidin-2-amine

Product 1

HCID 12043763N-(2-Amino-5-benzyl-6-methylpyrimidine-4-yl)-N-pentylamineYield 89.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-benzyl-4-chloro-6-methylpyrimidine-2-ylamine (500 mg, 2.14 mmol), amylamine (1.24 ml) and dioxane (4 ml) was kept at 95-100° C. for 19 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, and concentrated in vacuo. The residue was purified by silica gel column chromatography (2% MeOH/CHCl3) to give the object compound (546 mg, 89.7%).

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. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (2% MeOH/CHCl3)

Sources & evidence

ORD record
ord-9f103579a5974a6dbb5baa6adf201994
Source dataset
uspto-grants-2005_10
Patent number
US06951866B2

Linked notes

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