Dichloromethane → HCID 178433135, compound

HRID 1371111Notes

Reaction equation

HRID 1371111 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][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][NH2:22].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>O>[CH3:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][NH:22][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

6

Reactant 4

HCID 6344DichloromethaneHCID 69932-MethylbenzylamineHCID 11430Potassium CarbonateHCID 178432852HCID 178432852, compound

Product 1

HCID 178433135HCID 178433135, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
140 °C

Procedure

To a mixture of 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (85.0 mg, 0.35 mmol) and 2-methylbenzyl amine (Aldrich Chemical Company) (2.2 mL, 17.4 mmol) was added a solution of K2CO3 (0.35 g, 2.54 mmol) in H2O (2.5 mL). This mixture was stirred at 140° C. in a closed-capped Wheaton vial for 1.5 h. After cooling, CH2Cl2 (10 mL) and H2O (10 mL) were added. The organic solution was removed and the aqueous solution washed with CH2Cl2 (10 mL). The combined organic solutions were washed with saturated NaCl (15 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (3% MeOH:CHCl3 on silica gel) and then recrystallized from MeOH/CH2Cl2 to give 42 mg (35%) of the title compound as a white solid. Mp: 277-281° C. MS m/z: 329 (M+1). 1H NMR (DMSO-d6; 400 MHz): δ 2.38 (s, 3), 2.42 (s, 3), 4.69 (d, 2, J=4.8), 6.75 (s, 1), 6.98 (br t, 1), 7.19-7.25 (m, 3), 7.35-7.42 (m, 2), 7.49 (t, 2, J=7.8), 7.76 (d, 2, J=7.8), 11.27 (s, 1). Anal. Calcd for C21H20N4: C, 76.83; H, 6.10; N, 17.07. Found: C, 76.58; H, 6.20; N, 16.94.

Workup

  1. temperatureAfter cooling
  2. customThe organic solution was removed
  3. washthe aqueous solution washed with CH2Cl2 (10 mL)
  4. washThe combined organic solutions were washed with saturated NaCl (15 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (3% MeOH:CHCl3 on silica gel)
  9. customrecrystallized from MeOH/CH2Cl2

Sources & evidence

ORD record
ord-714dfd827bf04739b2d255a0ee4bad92
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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