Triethylamine → HCID 18326390, compound

HRID 1250656Notes

Reaction equation

HRID 1250656 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1.C(N(CC)CC)C.Cl.[C:21]([NH:25][NH2:26])([CH3:24])([CH3:23])[CH3:22]>CN(C=O)C>[C:21]([NH:25][NH:26][C:4]1[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=[C:2]([Cl:1])[N:3]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81889tert-Butylhydrazine monohydrochlorideHCID 71470642,4-Dichloro-7-methylthieno(3,2-d)pyrimidine

Product 1

HCID 18326390HCID 18326390, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 6 ml of a solution of 438 mg (2.0 mol) of 2,4-dichloro-7-metylthieno[3,2-d]pyrimidine and 445 mg (4.4 mmol) of triethylamine in DMF was added 249 mg (2.0 mmol) of t-butylhydrazine hydrochloride under ice cooling. The reaction mixture was stirred at the same temperature for one hour and then allowed to resume room temperature, followed by stirring for further 16 hours. After completion of the reaction, ice water was added to the reaction mixture, followed by extraction with ethyl acetate (50 ml×3). After the organic layer was washed successively with 1N hydrochloric acid, water and brine and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1:2) to give 314 mg (yield: 58.0%) of the title compound.

Workup

  1. customto resume room temperature
  2. stirringby stirring for further 16 hours
  3. additionwas added to the reaction mixture
  4. extractionfollowed by extraction with ethyl acetate (50 ml×3)
  5. washAfter the organic layer was washed successively with 1N hydrochloric acid, water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1:2)

Sources & evidence

ORD record
ord-32345096758e4085b1781180493b83bc
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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