Butylethylamine → HCID 21912301, compound

HRID 1831625Notes

Reaction equation

HRID 1831625 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]([CH3:19])[C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])[C:3]=1[CH3:20].[CH2:21]([NH:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24]>CS(C)=O>[CH2:21]([N:25]([CH2:26][CH3:27])[C:2]1[C:3]([CH3:20])=[C:4]([N:9]([CH3:19])[C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])[N:5]=[C:6]([CH3:8])[N:7]=1)[CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 25914ButylethylamineHCID 21912281HCID 21912281, compound

Product 1

HCID 21912301HCID 21912301, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of (6-chloro-2,5-dimethyl-pyrimidin-4-yl)-methyl-(2,4,6-trimethylphenyl)-amine (200 mg) and N-butyl-ethylamine (0.3 ml) in 1 ml of DMSO was heated in oil bath of 160° C. for 15 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give the crude material. After silica gel column purification using chloroform as eluent, the title compound was obtained as an oil. 1H NMR (CDCl3) δ 6.83 (s, 2H), 3.22 (s, 3H), 3.12 (m, 4H), 2.44 (s, 3H), 2.26 (s, 3H), 2.01 (s, 6H), 1.35–1.42 (m, 2H), 1.1–1.25(m, 2H), 1.00 (t, 3H), 0.90 (t, 3H) ppm.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customto give the crude material
  7. customAfter silica gel column purification

Sources & evidence

ORD record
ord-b83c2420953c42058a06797eb49d6421
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

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