Triethylamine → 2-Indanylamino-1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidine

HRID 48409Notes

Reaction equation

HRID 48409 reaction equation
Cl[C:2]1[C:3]2[N:10]([CH3:11])[N:9]=[C:8]([CH3:12])[C:4]=2[N:5]=[CH:6][N:7]=1.N[CH:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15]1.C([N:25](CC)CC)C>C(Cl)Cl>[CH:15]1([NH:25][N:9]2[CH:8]([CH3:12])[C:4]3[N:5]=[CH:6][N:7]=[CH:2][C:3]=3[N:10]2[CH3:11])[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 763102-AminoindaneHCID 133384107-Chloro-1,3-dimethyl-1H-pyrazolo(4,3-d)pyrimidine

Product 1

HCID 867593802-Indanylamino-1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidineYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-chloro-1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidine (28 mg, 0.15 mmol) (see J. Med. Chem. 31, 454 (1988)), 2-aminoindan (66 mg, 0.50 mmol), and triethylamine (30 μl, 0.2 mmol) in dry methylene chloride (1 ml) were heated to reflux for 2 hours. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=1:4) to obtain the title compound (26 mg, 0.093 mmol) having the following physical properties:

Workup

  1. temperatureto reflux for 2 hours
  2. customThe residue obtained
  3. distillationby distilling off the solvent under reduced pressure
  4. customwas purified by silica gel chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-0673ed38555c4ff0af02a036247a3b82
Source dataset
uspto-grants-2004_03
Patent number
US06703421B1

Reaction notes

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