Potassium Carbonate → HCID 178433064, compound

HRID 1371105Notes

Reaction equation

HRID 1371105 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[CH2:22][CH2:21][CH2:20][CH2:19]1.C([O-])([O-])=O.[K+].[K+]>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[CH2:22][CH2:21][CH2:20][CH2:19]2)[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 178432852HCID 178432852, compound

Product 1

HCID 178433064HCID 178433064, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This compound was prepared according to the method described in Example 2 by employing 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (70 mg, 0.287 mmol), pyrrolidine (Aldrich Chemical Company) (0.12 mL, 1.44 mmol) and K2CO3 (0.397 g, 2.87 mmol) in H2O (2 mL). The crude material was purified by flash chromatography on silica gel with 20:1 CHCl3:MeOH as eluant to give 42.1 mg (53%) of the title compound as an off-white solid. An analytical sample was obtained by recrystallization from EtOH. 1H NMR (CDCl3; 500 MHz): δ 2.07 (t, 4, J=6.3), 2.58 (s, 3), 3.88-3.90 (m, 4), 6.71 (s, 1), 7.36-7.46 (m, 3), 7.63 (d, 2, J=7.7). MS m/z: 279.5 (M+1), 277.5 (M−1). HRMS: Calcd for M+H: 279.1610. Found: 279.1613.

Workup

  1. customThis compound was prepared
  2. customThe crude material was purified by flash chromatography on silica gel with 20:1 CHCl3

Sources & evidence

ORD record
ord-52c454a1d304432c988ff441f02f54ba
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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