Benzylamine → HCID 178440418, compound

HRID 19592Notes

Reaction equation

HRID 19592 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.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)CCC>[CH2:15]([NH:22][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)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 178440413HCID 178440413, compound

Product 1

HCID 178440418HCID 178440418, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

5,7-Dichloro-3-isopropylpyrazolo[4,3-d]pyrimidine (1.015 mmol; 234.6 mg), 1 mL benzylamine and n-butanol (2 mL) were stirred at 65° C. for 4 hours. The reaction mixture was evaporated to dryness in vacuo. The residue was chromatographed on silica gel eluted with the following solvent system: CHCl3/MeOH (99/1), to give 7-benzylamino-5-chloro-3-isopropylpyrazolo[4,3-d]pyrimidine. Yield 96%; MS (ES+): 302.3 (100%, M+H+), 304.3 (32%, M+H+). 1H NMR (CDCl3; 300 MHz): 1.37 d (6H, J=7.1 Hz); 3.39 sept (1H, J=7.1 Hz), 6.72 s (1H), 4.82 s (2H), 7.28 m (5H).

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-9c4139e07311426983301652ac1c42cd
Source dataset
uspto-grants-2010_06
Patent number
US07745450B2

Reaction notes

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