N,N'-Dimethylethylenediamine → HCID 178484276, compound

HRID 635647Notes

Reaction equation

HRID 635647 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][CH2:21][NH:22][CH3:23].C([O-])([O-])=O.[K+].[K+]>O>[CH3:18][N:19]([CH2:20][CH2:21][NH:22][CH3:23])[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 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 178432852HCID 178432852, compound

Product 1

HCID 178484276HCID 178484276, compoundYield 22%

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, 0.29 mmol), N,N′-dimethylethylenediamine (Aldrich Chemical Company) (0.15 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 9:1 CHCl3:MeOH as eluant to give 18.5 mg (22%) of the title compound as an off-white solid. An analytical sample was obtained by recrystallization from EtOH. 1H NMR (CDCl3; 400 MHz): δ 2.60 (s, 6), 3.04 (t, 2, J=4.5), 3.15 (s, 3), 3.75 (t, 2, J=4.5), 6.76 (s, 1), 7.31-7.42 (m, 3), 7.70 (d, 2, J=7.4). MS m/z: 296 (M+1), 294 (M−1). HRMS: Calcd for M+H: 296.1875. Found: 296.1884.

Workup

  1. customThis compound was prepared
  2. customThe crude material was purified by flash chromatography on silica gel with 9:1 CHCl3

Sources & evidence

ORD record
ord-1801e7d55b7a44d8baceb65f534d152e
Source dataset
uspto-grants-2001_02
Patent number
US06187777B1

Reaction notes

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