Dichloromethane → HCID 178433140, compound

HRID 1371110Notes

Reaction equation

HRID 1371110 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[O:23][C:22]([CH2:24][NH2:25])=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>O>[CH3:18][C:19]1[O:23][C:22]([CH2:24][NH:25][C:2]2[N:7]=[C:6]([CH3:8])[NH:5][C:4]3[C:3]=2[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=3)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27246835-Methyl-2-furylmethylamineHCID 178432852HCID 178432852, compound

Product 1

HCID 178433140HCID 178433140, compoundYield 62%

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)) (47.6 mg, 0.19 mmol) and 5-methyl-2-furanmethanamine (Acros Chemical Company) (100 μL, 0.98 mmol) was added a solution of K2CO3 (0.11 g, 0.76 mmol) in H2O (1.5 mL). This mixture was stirred at 140° C. in a closed-capped Wheaton vial for 2.5 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) to give 37 mg (62%) of the title compound as a beige solid. Mp: 125-127.5° C. MS m/z: 319 (M+1), 294, 225, 195, 147. 1H NMR (CD3OD, 400 MHz): δ 2.28 (s, 3), 2.53 (s, 3), 4.72 (s, 2), 5.97 (d, 1, J=3.0), 6.24 (d, 1, J=3.0), 6.66 (s, 1), 7.34 (m, 1), 7.43 (t, 2, J=7.7), 7.71 (dd, 2, J=7.1, 1.4). HRMS: Calcd for M+H, C19H18ON4: 319.1555. Found: 319.1566.

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)

Sources & evidence

ORD record
ord-a8c41ea08c094b7babd7aafd23e9d327
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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