3-Chloroaniline → 7-(3-Chloroanilino)-5-chloro-3-isopropylpyrazolo[4,3-d]pyrimidine

HRID 19593

Reaction equation

HRID 19593 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[NH:10][N:9]=[C:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19]>C(N(C(C)C)CC)(C)C>[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH:19][C:4]1[C:5]2[NH:10][N:9]=[C:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=[C:2]([Cl:1])[N:3]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 178440413HCID 178440413, compound

Product 1

HCID 1784404177-(3-Chloroanilino)-5-chloro-3-isopropylpyrazolo[4,3-d]pyrimidineYield 16%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

5,7-Dichloro-3-isopropylpyrazolo[4,3-d]pyrimidine (90 mg), 1.2 mL of 3-chloroaniline and 250 μL of diisopropyl ethylamine were stirred at 60° C. for 24 hours. The reaction mixture was evaporated to dryness in vacuo. The residue was chromatographed on silica gel eluted with the following solvent system: CHCl3/heptane (100/17), to give 7-(3-chloroanilino)-5-chloro-3-isopropylpyrazolo[4,3-d]pyrimidine, yield 16%, mp=257-259° C. MS (ES+): 322.3 (100%, M+H+), 324.3 (64%, M+H+). 1H NMR (CDCl3; 300 MHz): 1.54 d (6H, J=7.1 Hz); 3.60 sept (1H, J=7.1 Hz), 7.16 d (1H), 7.34 t (1H), 7.88 d (1H), 8.10 s (1H).

Workup

  1. customThe reaction mixture was evaporated to dryness in vacuo
  2. customThe residue was chromatographed on silica gel
  3. washeluted with the following solvent system

Sources & evidence

ORD record
ord-8f8c352671c94590927e6ea4b4fc753b
Source dataset
uspto-grants-2010_06
Patent number
US07745450B2

Linked notes

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