1-Isopropyl-3-methyl-1H-pyrazol-5-amine → Ethyl 6-cyclopropyl-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 476040Notes

Reaction equation

HRID 476040 reaction equation
[CH:1]1([C:4](=O)[CH2:5][C:6](=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[CH3:14][C:15]1[CH:19]=[C:18]([NH2:20])[N:17]([CH:21]([CH3:23])[CH3:22])[N:16]=1>C1C=CC=CC=1>[CH:1]1([C:4]2[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:19]3[C:15]([CH3:14])=[N:16][N:17]([CH:21]([CH3:23])[CH3:22])[C:18]=3[N:20]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 1210181-Isopropyl-3-methyl-1H-pyrazol-5-amineHCID 16779961Ethyl 4-cyclopropyl-2,4-dioxobutanoate

Product 1

HCID 67124269Ethyl 6-cyclopropyl-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of ethyl 4-cyclopropyl-2,4-dioxobutanoate (700 mg, 3.76 mmol), 3-methyl-1-(1-methylethyl)-1H-pyrazol-5-amine (523 mg, 3.76 mmol) and benzene (20 mL) were heated at 65° C. for 6 hr, and then allowed to cool to room temperature for 2 d. The solvent was removed under reduced pressure and the residue purified via silica gel chromatography (eluent: 0 to 25% EtOAc:Hex). The final product was collected as 0.77 g (71%). LCMS E-S (M+H)=288.0. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.04-1.11 (m, 2H), 1.13-1.20 (m, 4H), 1.47 (t, J=7.20 Hz, 6H), 1.55 (d, J=6.82 Hz, 12H), 2.16-2.25 (m, 2H), 2.68 (s, 6H), 4.49 (q, J=7.07 Hz, 4H), 5.20 (spt, J=6.78 Hz, 2H), 7.41 (s, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified via silica gel chromatography (eluent: 0 to 25% EtOAc:Hex)
  3. customThe final product was collected as 0.77 g (71%)

Sources & evidence

ORD record
ord-a065ccefbf2b48bd9725ec2fd3a9b33b
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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