Potassium Carbonate → HCID 178433075, compound

HRID 1371116Notes

Reaction equation

HRID 1371116 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][CH2:21][CH:20]([CH2:24][OH:25])[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[CH2:23][CH2:22][CH2:21][CH:20]([CH2:24][OH:25])[CH2:19]2)[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 107308Piperidin-3-ylmethanolHCID 178432852HCID 178432852, compound

Product 1

HCID 178433075HCID 178433075, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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), 3-piperidinemethanol (Aldrich Chemical Company) (0.241 g, 2.09 mmol) and K2CO3 (0.34 g, 2.50 mmol) in H2O (2.5 mL) to obtain crude pink solids. Recrystallization from EtOH/MeOH gave 0.040 g (30%) of the title compound as an off-white solid. Mp: 255-256° C. 1H NMR (DMSO-d6; 500 MHz): δ 1.45 (m, 1), 1.59 (m, 1), 1.67 (m, 1), 1.83 (m, 2), 2.42 (s, 3), 3.47 (m, 2), 3.55 (m, 1), 3.68 (m, 2), 3.86 (m, 1), 5.44 (br s, 1), 6.77 (s, 1), 7.38 (m, 1), 7.47 (m, 2), 7.87 (d, 2, J=7.2), 11.24 (br s, 1). MS m/z: 321 (M−1).

Workup

  1. customThis compound was prepared
  2. customto obtain crude pink solids
  3. customRecrystallization from EtOH/MeOH

Sources & evidence

ORD record
ord-7d3637eececc433f81517667579021c1
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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