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

HRID 989707

Reaction equation

HRID 989707 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-0c51ed97379a4340923c28e477daca0e
Source dataset
uspto-grants-2002_10
Patent number
US06458798B1

Linked notes

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