Piperazine → HCID 178433086, compound

HRID 1371117Notes

Reaction equation

HRID 1371117 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]=12.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C([O-])([O-])=O.[K+].[K+]>O.CCOC(C)=O>[CH3:8][C:6]1[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]2=[C:2]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[N:7]=1

Participants

6

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 178432852HCID 178432852, compound

Product 1

HCID 178433086HCID 178433086, compoundYield 29.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared according to the method described in Example 26 by employing 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (0.10 g, 0.41 mmol), piperazine (Aldrich Chemical Company) (0.382 g, 4.43 mmol) and K2CO3 (0.34 g, 2.50 mmol) in H2O (2.5 mL) to give crude pink solids. These solids were taken up in hot EtOAc, cooled to room temperature, and the impurities were removed by filtration. The filtrate was concentrated to give 0.035 g (29%) of the title compound as an off-white solid. Mp: 236° C. 1H NMR (DMSO-d6; 500 MHz): δ 2.42 (s, 3), 2.85 (t, 4, J=5.2), 3.62 (t, 4, J=5.2), 6.77 (s, 1), 7.36 (m, 1), 7.45 (t, 2, J=7.8), 7.95 (d, 2, J=7.6), 10.96 (s, 1); MS m/z: 294 (M+1). Anal. Calcd for C17H19N5O.0.5H2O: C, 67.53; H, 6.67; N, 23.16. Found: C, 67.35; H, 6.59; N, 23.01.

Workup

  1. customThis compound was prepared
  2. customto give crude pink solids
  3. customthe impurities were removed by filtration
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-14b977dba4194706b8e9bfc7c38cd904
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

Loading…