Potassium Carbonate → HCID 178467835, compound

HRID 1371119Notes

Reaction equation

HRID 1371119 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]([O:20][CH2:21][CH2:22][CH2:23][NH2:24])[CH3:19].C([O-])([O-])=O.[K+].[K+]>O>[CH2:18]([O:20][CH2:21][CH2:22][CH2:23][NH:24][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)[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22720Propanolamine ethyl etherHCID 178432852HCID 178432852, compound

Product 1

HCID 178467835HCID 178467835, compoundYield 44%

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) with 3-ethoxypropylamine (Aldrich Chemical Company) (0.225 g, 2.18 mmol) and K2CO3 (0.34 g, 2.50 mmol) in H2O (2.5 mL) to give a biphasic reaction mixture, which was partitioned between CH2Cl2 and H2O. The organic layers were separated, dried over MgSO4 and concentrated. The resulting yellow oil was purified by flash chromatography on silica gel (1:40 MeOH/CH2Cl2 followed by 1:20 MeOH/CH2Cl2 as eluant) to give 0.056 g (44%) of the title compound as a light yellow oil that solidified upon standing. Mp: 208-209.5° C. 1H NMR (CDCl3; 500 MHz): δ 1.16 (t, 3, J=7.0), 1.99 (quin, 2, J=5.8, 6.4), 2.58 (s, 3), 3.52 (q, 2, J=7.1), 3.63 (t, 2, J=5.6), 3.74 (t, 2, J=6.6), 5.95 (br s, 1), 6.67 (s, 1), 7.33 (t, 1, J=7.4), 7.40 (t, 2, J=7.6), 7.66 (d, 2, J=7.6); MS m/z: 311 (M+1).

Workup

  1. customThis compound was prepared
  2. customto give
  3. customa biphasic reaction mixture, which
  4. customwas partitioned between CH2Cl2 and H2O
  5. customThe organic layers were separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe resulting yellow oil was purified by flash chromatography on silica gel (1:40 MeOH/CH2Cl2 followed by 1:20 MeOH/CH2Cl2 as eluant)

Sources & evidence

ORD record
ord-1a2f82ff527f42699471754d7d3a7d42
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

Loading…