Potassium Carbonate → HCID 178433077, compound

HRID 1371104Notes

Reaction equation

HRID 1371104 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][CH:20]([OH:23])[CH2:19]1.C([O-])([O-])=O.[K+].[K+]>O>[CH3:8][C:6]1[NH:5][C:4]2[C:3]([N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=2)=[C:2]([N:18]2[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19]2)[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 982104-HydroxypyrrolidineHCID 178432852HCID 178432852, compound

Product 1

HCID 178433077HCID 178433077, compoundYield 37%

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)) (70.0 mg, 0.29 mmol), 3-pyrrolidinol (Aldrich Chemical Company) (0.12 mL, 1.44 mmol) and K2CO3 (0.40 g, 2.87 mmol) in H2O (2 mL). The crude material was purified by flash chromatography on silica gel with 10:1 CHCl3:MeOH as eluant to give 30.9 mg (37%) of the title compound as an off-white solid. An analytical sample was obtained by recrystallization from EtOH. Mp: 234-235° C. 1H NMR (DMSO-d6; 500 MHz): δ 1.96-2.05 (m, 2), 2.39 (s, 3), 3.77-3.93 (m, 4), 4.43 (s, 1), 5.03 (s, 1), 6.71 (s, 1), 7.38-7.50 (m, 3), 7.88 (d, 2, J=7.6), 10.64 (br s, 1). MS m/z: 295 (M+1), 293 (M−1). HRMS: Calcd for M+H: 295.1923. Found: 295.1910.

Workup

  1. customThis compound was prepared
  2. customThe crude material was purified by flash chromatography on silica gel with 10:1 CHCl3

Sources & evidence

ORD record
ord-61646f422c734ce2a610616603809f87
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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