1-Phenylpiperazine → HCID 178433085, compound

HRID 635703Notes

Reaction equation

HRID 635703 reaction equation
[CH3:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[NH:10][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:8][C:6]=2[N:7]=1.[C:18]1([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH3:1][C:2]1[NH:7][C:6]2=[CH:8][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:10][C:5]2=[C:4]([N:27]2[CH2:28][CH2:29][N:24]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:25][CH2:26]2)[N:3]=1

Participants

3

Reactant 2

HCID 70961-PhenylpiperazineHCID 10728948HCID 10728948, compound

Product 1

HCID 178433085HCID 178433085, compoundYield 54%

Conditions

Temperature
140 °C

Procedure

A mixture of 2-methyl-4-chloro-6-phenyl-5H-pyrrolo[3,2-d]pyrimidine (Example 1(e)) (0.51 g, 2.45 mmol) and 1-phenylpiperazine (Aldrich Chemical Company) (10 mL) was stirred at 140° C. for 4 h under a N2 atmosphere. After cooling the precipitate was removed by filtration and the filtrate was poured onto a mixture of CH2Cl2 (30 mL) and H2O (40 mL). The mixture was transferred to a separatory funnel where the organic solution was collected, washed with H2O (3×40 mL), saturated NaCl (50 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel with 97:3 CHCl3/MeOH as eluant to give 483 mg (54%) of 2-methyl-6-phenyl-4-(4-phenylpiperazinyl)pyrrolo[3,2-d]pyrimidine as a tan colored solid. This compound (483 mg, 1.31 mmol) was dissolved in 5:1 EtOAc/MeOH (30 mL) and heated to boiling. To the hot solution was added 1 M ethereal HCl (1.30 mL, 1.30 mmol). The solution was allowed to cool to room temperature. The resulting solid was collected by filtration, washed with EtOAc (2×5 mL), Et2O (2×5 mL) and dried under vacuum at 60° C. to give 404 mg (41%) of the title compound as a beige powder. Mp: 232-234.5° C. 1H NMR (DMSO-d6; 500 MHz): δ 2.55 (s, 3), 3.36 (br s, 4), 4.21 (br s, 4), 6.80 (t, 1, J=7.2), 6.88 (s, 1), 6.99 (d, 2, J=7.8), 7.22 (t, 2, J=7.5), 7.46 (q, 1, J=7.1), 7.51 (t, 2, J=7.3), 7.93 (d, 2, J=7.7), 12.06 (s, 1), 14.46 (s, 1). MS m/z: 370 (M+1 for free base). Anal. Calcd for C23H23N5.2.0HCl.2.5H2O: C, 56.67; H, 6.20; N, 14.37; Cl, 14.55. Found: C, 56.67; H, 6.23; N, 14.19; Cl, 14.34.

Workup

  1. temperatureAfter cooling the precipitate
  2. customwas removed by filtration
  3. additionthe filtrate was poured onto a mixture of CH2Cl2 (30 mL) and H2O (40 mL)
  4. customThe mixture was transferred to a separatory funnel
  5. customwhere the organic solution was collected
  6. washwashed with H2O (3×40 mL), saturated NaCl (50 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography on silica gel with 97:3 CHCl3/MeOH as eluant

Sources & evidence

ORD record
ord-646a9cf0bce3464db4603834a8f9908c
Source dataset
uspto-grants-2001_02
Patent number
US06187777B1

Reaction notes

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