Potassium Carbonate → HCID 14653258, compound

HRID 893310Notes

Reaction equation

HRID 893310 reaction equation
Br[CH2:2][C:3]1[N:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:5](=[O:16])[C:6]2[CH:11]=[C:10]([S:12](=[O:15])(=[O:14])[NH2:13])[S:9][C:7]=2[N:8]=1.[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:4]1[C:5](=[O:16])[C:6]2[CH:11]=[C:10]([S:12](=[O:15])(=[O:14])[NH2:13])[S:9][C:7]=2[N:8]=[C:3]1[CH2:2][N:28]1[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 14653254HCID 14653254, compound

Product 1

HCID 14653258HCID 14653258, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To 5.0 g of 3,4-dihydro-2-bromomethyl-3-(2-chlorophenyl)-4-oxo-6-sulfamoylthieno[2,3-d]pyrimidine were added 50 ml of dimethylformamide, 1.5 g of N-methylpiperazine and 3.2 g of potassium carbonate, and the mixture was stirred at 40° C. for 1.5 hours. The reaction mixture was poured onto water, and the mixture was extracted with ethyl acetate. The concentrated residue of the extract was crystallized from ethanol, followed by recrystallization of the obtained crystals from methanol-chloroform to afford 1.9 g of the title compound, m.p. 233.5°-234° C. (decomposition). The hydrochloric thereof showed m.p. of 246°-247° C. (decomposition).

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe concentrated residue of the extract was crystallized from ethanol
  4. customfollowed by recrystallization of the obtained crystals from methanol-chloroform

Sources & evidence

ORD record
ord-e3e0029c09ce4bb4ae8adfb5f87d084d
Source dataset
uspto-grants-1992_06
Patent number
US05124331

Reaction notes

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