3-Pentanamine → (1-Ethyl-propyl)-[5-methyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-amine

HRID 2183537Notes

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]([CH:23]([NH2:26])[CH2:24][CH3:25])[CH3:22]>CN1CCCC1=O>[CH2:21]([CH:23]([NH:26][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)[CH2:24][CH3:25])[CH3:22]

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 7-chloro-5-methyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (190 mg, 0.63 mmol) and 1-ethylpropylamine (4 ml) in 1 ml of N-methylpyrrolidinone was heated at 125° C. oil bath for 15 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 chloroform to 2% methanol in chloroform as eluent to give 195 mg (87%) of the title compound as a green solid. 1H NMR (CDCl3) ä 7.87(s, 1H), 6.97(s, 2H), 6.12(d, 1H), 5.85(s, 1H), 3.52(m, 1H), 2.48(s, 3H), 2.09(s, 3H), 2.16(s, 6H), 1.6-1.9(m, 4H), 1.05(t, 6H)ppm.

Workup

customThe mixture was quenched with water
extractionextracted with ethyl acetate
customThe organic layer was dried
concentrationconcentrated
custompurified through silica gel column chromatography

Sources & evidence

ORD record: ord-d51451899d2f4d3893f65194bf93824d
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900217B2

Reaction notes

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