Dichloromethane → HCID 178433159, compound

HRID 1371108Notes

Reaction equation

HRID 1371108 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.[F:18][C:19]([F:23])([F:22])[CH2:20][NH2:21].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>O>[CH3:8][C:6]1[NH:5][C:4]2[C:3]([N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=2)=[C:2]([NH:21][CH2:20][C:19]([F:23])([F:22])[F:18])[N:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 11430Potassium CarbonateHCID 178432852HCID 178432852, compound

Product 1

HCID 178433159HCID 178433159, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
140 °C

Procedure

To a mixture of 4-chloro-2-methyl-6-phenyl-pyrrolo[3,2-d]pyrimidine (Example-1(e)) (55.9 mg, 0.23 mmol) and 2,2,2-trifluoroethylamine (Aldrich Chemical Company) (95 μL, 1.15 mmol) was added a solution of K2CO3 (0.13 g, 0.92 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 was washed with CH2Cl2 (10 mL). The combined organic solutions were washed with saturated aqueous NaCl (15 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was washed with CH2Cl2 until all the color was removed. The remaining solid was recrystallized from hot MeOH to provide 21 mg (29%) of the title compound as a white solid. Mp: >310° C. MS m/z 307 (M+1), 294, 281, 226. 1H NMR (DMSO-d6; 400 MHz): δ 2.31 (s, 3), 2.52 (s, 2), 6.74 (s, 1), 7.33 (t, 1, J=7.3), 7.43 (t, 2, J=7.8), 7.92 (d, 2, J=7.3), 11.74 (s, 1), 12.22 (s, 1). HRMS: Calcd for M+H, C15H13F3N4: 307.1168. Found: 307.1160.

Workup

  1. temperatureAfter cooling
  2. customThe organic solution was removed
  3. washthe aqueous solution was washed with CH2Cl2 (10 mL)
  4. washThe combined organic solutions were washed with saturated aqueous NaCl (15 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. washThe residue was washed with CH2Cl2 until all the color
  9. customwas removed
  10. customThe remaining solid was recrystallized from hot MeOH

Sources & evidence

ORD record
ord-97f05216a0a14abe941d2e55240bd7e5
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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