Allylamine → HCID 18326503, compound

HRID 1250657Notes

Reaction equation

HRID 1250657 reaction equation
[C:1]([NH:5][NH:6][C:7]1[C:8]2[S:16][CH:15]=[C:14]([CH3:17])[C:9]=2[N:10]=[C:11](Cl)[N:12]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:18]([NH2:21])[CH:19]=[CH2:20].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.CCCCCC>[CH2:18]([NH:21][C:11]1[N:12]=[C:7]([NH:6][NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:8]2[S:16][CH:15]=[C:14]([CH3:17])[C:9]=2[N:10]=1)[CH:19]=[CH2:20]

Participants

5

Reactant 3

HCID 7853AllylamineHCID 516892Sodium BicarbonateHCID 18326390HCID 18326390, compound

Product 1

HCID 18326503HCID 18326503, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

270 mg (1.0 mmol) of 4-(2-t-butylhydrazino)-2-chloro-7-methylthieno[3,2-d]pyrimidine and 914 mg (16.0 mmol) of allylamine were heated in a sealed tube at 140° C. for 16 hours. After completion of the reaction, the reaction mixture was allowed to resume room temperature, followed by adding a saturated aqueous sodium hydrogen carbonate solution thereto and extraction with ethyl acetate (50 ml×2). After the organic layer was washed with brine and dried over anhydrous sodium sulfate, the solvent was distilled off. The residue was purified by a silica gel chromatography (eluent: ethyl acetate-hexane=1/4] to give 92 mg (yield: 31.6%) of the title compound.

Workup

  1. customAfter completion of the reaction
  2. customto resume room temperature
  3. extractionextraction with ethyl acetate (50 ml×2)
  4. washAfter the organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by a silica gel chromatography (eluent

Sources & evidence

ORD record
ord-be2530f5e5204891a8e831ebb260acc9
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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