1,5-Dimethyl-1H-pyrazol-4-amine dihydrochloride → (3R)-1-(2-((1,5-dimethyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-3-ethyl-2-oxopyrrolidine-3-carbonitrile

HRID 714871Notes

Reaction equation

HRID 714871 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][C@:10]([CH2:15][CH3:16])([C:13]#[N:14])[C:9]2=[O:17])[CH:5]=[CH:4][N:3]=1.Cl.Cl.[CH3:20][N:21]1[C:25]([CH3:26])=[C:24]([NH2:27])[CH:23]=[N:22]1>CC(O)C>[CH3:20][N:21]1[C:25]([CH3:26])=[C:24]([NH:27][C:2]2[N:7]=[C:6]([N:8]3[CH2:12][CH2:11][C@:10]([CH2:15][CH3:16])([C:13]#[N:14])[C:9]3=[O:17])[CH:5]=[CH:4][N:3]=2)[CH:23]=[N:22]1

Participants

4

Reactant 2

HCID 446309061,5-Dimethyl-1H-pyrazol-4-amine dihydrochlorideHCID 117840665(3R)-1-(2-chloropyrimidin-4-yl)-3-ethyl-2-oxopyrrolidine-3-carbonitrile

Product 1

HCID 117840341(3R)-1-(2-((1,5-dimethyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-3-ethyl-2-oxopyrrolidine-3-carbonitrileYield 69.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of (3R)-1-(2-chloropyrimidin-4-yl)-3-ethyl-2-oxopyrrolidine-3-carbonitrile (100 mg) obtained in Step A of Example 8 and 1,5-dimethyl-1H-pyrazol-4-amine dihydrochloride (73 mg) in propan-2-ol (4.0 mL) was stirred in a microwave reactor at 160° C. for 1 hr, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate), and recrystallized (diisopropyl ether/ethyl acetate) to give the title compound (90 mg).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)
  3. customrecrystallized (diisopropyl ether/ethyl acetate)

Sources & evidence

ORD record
ord-43d0344d68684cd3b55b16e4f49538b4
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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