Potassium Carbonate → HCID 178433152, compound

HRID 1371107Notes

Reaction equation

HRID 1371107 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.[CH3:18][NH:19][CH2:20][C:21]1[O:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>O>[O:25]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:20][N:19]([CH3:18])[C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2[C:3]=1[N:11]=[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:9]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78492N-MethylfurfurylamineHCID 178432852HCID 178432852, compound

Product 1

HCID 178433152HCID 178433152, compoundYield 59%

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), N-methylfurfurylamine (The Sigma-Aldrich Library of Rare Chemicals) (0.16 g, 1.44 mmol) and K2CO3 (0.40 g, 2.87 mmol) in H2O (2 mL). The crude material was purified by preparative TLC on silica gel with 1:1 EtOAc:hexanes as eluant to give 53.6 mg (59%) of the title compound as an off-white solid. An analytical sample was obtained by recrystallization from EtOAc. Mp: 168-169° C. 1H NMR (CDCl3; 500 MHz): δ 2.62 (s, 3), 3.35 (s, 3), 4.83 (s, 2), 6.42-6.44 (m, 2), 6.79 (s, 1), 7.36-7.48 (m, 4), 7.64 (d, 2, J=7.2), 8.91 (br s, 1). MS m/z: 319.5 (M+1), 317.0 (M−1). HRMS: Calcd for M+H: 319.1559. Found: 319.1566.

Workup

  1. customThis compound was prepared
  2. customThe crude material was purified by preparative TLC on silica gel with 1:1 EtOAc

Sources & evidence

ORD record
ord-e74bd3db6f0f4832a275f6060e9c1c5f
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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