N-methyl-2-pyrrolidone → [2,5-Dimethyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-ethyl-propyl-amine

HRID 2183539Notes

Reaction equation

HRID 2183539 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])=[C:6]2[N:5]=[C:4]([CH3:20])[CH:3]=1.[CH2:21]([NH:24][CH2:25][CH3:26])[CH2:22][CH3:23].[CH3:27]N1CCCC1=O>>[CH3:27][C:9]1[C:10]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[CH3:19])=[C:6]2[N:5]=[C:4]([CH3:20])[CH:3]=[C:2]([N:24]([CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])[N:7]2[N:8]=1

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 883981-Propanamine, N-ethyl-HCID 224743217-Chloro-5-methyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 10269356[2,5-Dimethyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-ethyl-propyl-amine

Conditions

Temperature
135 °C

Procedure

A mixture of 7-chloro-5-methyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (200 mg, 0.66 mmol) and N-propylethylamine (2 ml) in 1 ml of N-methylpyrrolidinone was heated at 135° C. oil bath for 4 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated and purified through silica gel column chromatography using hexane to 10% ethyl acetate in hexane as eluent to give 150 mg of the title compound as a clear green oil. 1H NMR (CDCl3) ä 6.95(s, 2H), 5.80(s, 1H), 3.85(q, 2H), 3.67(dd, 2H), 2.41(s, 3H), 2.32(s, 3H), 2.21(s, 3H), 2.03(s, 6H), 1.76(m, 2H), 1.29(t, 3H), 0.98(t, 3H) ppm.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. custompurified through silica gel column chromatography

Sources & evidence

ORD record
ord-8fb6188615d24b16aa40d56765eebe03
Source dataset
uspto-grants-2005_05
Patent number
US06900217B2

Reaction notes

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