Butylethylamine → HCID 9930552, compound

HRID 1813911Notes

Reaction equation

HRID 1813911 reaction equation
Cl[C:2]1[C:3]2[CH2:12][CH:11]([CH3:13])[C:10](=[O:14])[N:9]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.[CH2:24]([NH:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27]>CS(C)=O>[CH2:24]([N:28]([CH2:29][CH3:30])[C:2]1[C:3]2[CH2:12][CH:11]([CH3:13])[C:10](=[O:14])[N:9]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1)[CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 25914ButylethylamineHCID 22504340HCID 22504340, compound

Product 1

HCID 9930552HCID 9930552, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 4-chloro-2,6-dimethyl-8-(2,4,6-trimethyl-phenyl)-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one (75 mg, 0.227 mmol) and N-butyl-ethyl-amine (65 mg, 0.682 mmol) in DMSO (1 ml) was heated in an oil bath of 135° C. for 15 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give 114 mg of the crude material. Silica gel column purification using 5% ethyl acetate in hexane as eluent provided 50 mg of the title compound as a colorless oil. 1H NMR (CDCl3) δ 6.95 (s,1H), 6.94(s,1H), 3.2-3.55(m,4H), 2.88-3.05(dd,1H), 2.70-2.85(m,1H), 2.55-2.70(m,1H), 2.35(s,3H), 2.25(s,3H), 2.05(s,3H), 1.97(s,3H), 1.5-1.65(m,2H), 1.3-1.5(m,2H), 1.35(d,3H), 1.2(t,3H), 0.98(t,3H) ppm.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto give 114 mg of the crude material
  6. customSilica gel column purification

Sources & evidence

ORD record
ord-33ba6d9ba1b645b8b2f11dafa0ba3760
Source dataset
uspto-grants-2005_04
Patent number
US06875769B2

Reaction notes

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