Potassium Carbonate → HCID 25242055, compound

HRID 2102834Notes

Reaction equation

HRID 2102834 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[O:10][C:9]3[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:8]=3[C:6]=2[N:7]=1.C([O-])([O-])=O.[K+].[K+].[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>C(O)C.[OH-].[Na+]>[Cl:1][C:2]1[N:3]=[C:4]([N:27]2[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]2)[C:5]2[O:10][C:9]3[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:8]=3[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 24854610HCID 24854610, compound

Product 1

HCID 25242055HCID 25242055, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2,4,8-trichloro-benzo[4,5]furo[3,2-d]pyrimidine (1.0 g, 4.8 mmol) in ethanol (15 mL) was added K2CO3 (1.3 g, 9.6 mmol) followed by N-methylpiperazine (0.532 mL, 4.8 mmol). After 2 h, the reaction mixture was diluted with 1 N NaOH (30 mL) and extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with 1 N NaOH (20 mL), dried, and concentrated to afford the desired product (1.03 g, 77%). 1H NMR (CDCl3): 8.10 (s, 1H), 7.55-7.49 (m, 2H), 4.13-4.11 (m, 4H), 2.59-2.56 (m, 4H), 2.36 (s, 3H).

Workup

  1. extractionextracted with CH2Cl2 (3×20 mL)
  2. washThe combined organic layers were washed with 1 N NaOH (20 mL)
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-721ce4df969f4396a97095920108b388
Source dataset
uspto-grants-2009_08
Patent number
US07576092B2

Reaction notes

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