Potassium Carbonate → HCID 178449020, compound

HRID 1371106Notes

Reaction equation

HRID 1371106 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.[CH2:18]([NH:20][CH2:21][C:22]([CH3:24])=[CH2:23])[CH3:19].C([O-])([O-])=O.[K+].[K+]>O>[CH2:18]([N:20]([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)[CH2:21][C:22]([CH3:24])=[CH2:23])[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 875872-Propen-1-amine, N-ethyl-2-methyl-HCID 178432852HCID 178432852, compound

Product 1

HCID 178449020HCID 178449020, compoundYield 42%

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-ethyl-2-methylallylamine (Aldrich Chemical Company) (0.19 mL, 1.44 mmol) and K2CO3 (0.397 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 36.7 mg (42%) of the title compound as off-white solid. An analytical sample was obtained by recrystallization from EtOAc. Mp: 148-150° C. 1H NMR (CDCl3; 500 MHz): δ 1.32 (t, 3, J=7.1), 1.95 (s, 3), 2.59 (s, 3), 3.78 (q, 2, J=7.1), 4.20 (s, 2), 5.18 (s, 1), 5.24 (s, 1), 6.74 (s, 1), 7.35-7.48 (m, 3), 7.55 (d, 2, J=7.4), 8.47 (br s, 1). MS m/z: 307 (M+1), 305 (M−1). Anal. Calcd for C19H22N4: C, 74.48; H, 7.24; N, 18.28. Found: C, 74.36; H, 7.27; N, 18.19.

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-c749a57c0af7494f8cfbfb59c0224535
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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