2,4-Pentanedione, 3-benzyl- → 4-(4-Benzyl-3,5-dimethyl-pyrazol-1-yl)-6-pyridin-2-yl-[1,3,5]triazin-2-ylamine

HRID 1897007

Reaction equation

HRID 1897007 reaction equation
[NH:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:6]=[C:5]([NH2:15])[N:4]=1)[NH2:2].[CH2:16]([CH:23]([C:27](=O)[CH3:28])[C:24](=O)[CH3:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CS(C)=O.C(Cl)Cl.C(OCC)(=O)C>[CH2:16]([C:23]1[C:24]([CH3:25])=[N:2][N:1]([C:3]2[N:8]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=3)[N:6]=[C:5]([NH2:15])[N:4]=2)[C:27]=1[CH3:28])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 3

HCID 977572,4-Pentanedione, 3-benzyl-HCID 521998p-Toluenesulfonic acid monohydrateHCID 6089524-Hydrazinyl-6-(pyridin-2-yl)-1,3,5-triazin-2-amine

Product 1

HCID 221748704-(4-Benzyl-3,5-dimethyl-pyrazol-1-yl)-6-pyridin-2-yl-[1,3,5]triazin-2-ylamine

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of 4-hydrazino-6-pyridin-2-yl-[1,3,5]triazin-2-ylamine (5.25 g, 25.6 mmol), 3-benzylpentane-2,4-dione (5.0 g, 28.4 mmol), and p-toluenesulfonic acid monohydrate (0.475 g, 2.50 mmol) in dimethylsulfoxide (50 mL) was heated to 75° C. for 20 hours. The reaction mixture was allowed to cool to room temperature, and the suspension was dissolved in methylene chloride (700 mL). The solution was washed three times with water, once with brine, dried (magnesium sulfate), and concentrated to afford a moist solid. The crude product was suspended in ethyl acetate (50 mL), heated to reflux, allowed to cool to room temperature, and filtered (repeated three times). The final product was obtained as a white solid containing 3% dimethylsulfoxide by weight: 8.63 g (90%). 1H NMR (CDCl3) δ 8.84-8.53 (m, 1H), 8.48 (d, J=7.9 Hz, 1H), 7.86-7.91 (m, 1H), 7.46-7.50 (m, 1H), 7.13-7.30 (m, 5H), 6.61 (br s, 1H), 6.40 (br s, 1H), 3.83 (s, 2H), 2.79 (s, 3H), 2.24 (s, 3H) ppm. MS (ESI) m/z 358 (M+H+).

Workup

  1. temperatureto cool to room temperature
  2. washThe solution was washed three times with water
  3. dry with materialonce with brine, dried (magnesium sulfate)
  4. concentrationconcentrated
  5. customto afford a moist solid
  6. temperatureheated
  7. temperatureto reflux
  8. temperatureto cool to room temperature
  9. filtrationfiltered (repeated three times)

Sources & evidence

ORD record
ord-1b737053ca0a48c0bcb7b8c98ae7615d
Source dataset
uspto-grants-2013_08
Patent number
US08518999B2

Linked notes

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