Pentylamine → HCID 12043764, compound

HRID 989708Notes

Reaction equation

HRID 989708 reaction equation
[CH2:1]([C:8]1[C:9](Cl)=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([NH2:21])[CH2:17][CH2:18][CH2:19][CH3:20]>O1CCOCC1>[NH2:14][C:11]1[N:10]=[C:9]([NH:21][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 8060PentylamineHCID 22313252HCID 22313252, compound

Product 1

HCID 12043764HCID 12043764, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-benzyl-4-chloropyrimidine-2-ylamine (350 mg, 0.74 mmol), amylamine (0.74 ml) and dioxane (4 ml) was kept at 90-100° C. for 8 hours. The reaction mixture was concentrated in vacuo, and the residue was extracted with ether and a saturated aqueous NaHCO3 solution. The organic layer was washed with saturated brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (MeOH:CHCl3=70:1) to give the object compound (355 mg, 82.2%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionthe residue was extracted with ether
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (MeOH:CHCl3=70:1)

Sources & evidence

ORD record
ord-ad7112e2dc2348aa82007a34999198cd
Source dataset
uspto-grants-2002_10
Patent number
US06458798B1

Reaction notes

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