Propylamine → HCID 18326460, compound

HRID 1250651Notes

Reaction equation

HRID 1250651 reaction equation
[CH2:1]([NH:4][C:5]1[C:6]2[S:14][CH:13]=[C:12]([CH3:15])[C:7]=2[N:8]=[C:9](Cl)[N:10]=1)[CH:2]=[CH2:3].[CH2:16]([NH2:19])[CH2:17][CH3:18].C(=O)([O-])O.[Na+]>>[CH2:1]([NH:4][C:5]1[C:6]2[S:14][CH:13]=[C:12]([CH3:15])[C:7]=2[N:8]=[C:9]([NH:19][CH2:16][CH2:17][CH3:18])[N:10]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 7852PropylamineHCID 516892Sodium BicarbonateHCID 18326500HCID 18326500, compound

Product 1

HCID 18326460HCID 18326460, compoundYield 60%

Procedure

288 mg (1.2 mmol) of 4-allylamino-2-chloro-7-methylthieno[3,2-d]pyrimidine and 1.13 mg (19.2 mmol) of propylamine were heated in a sealed tube at 160° 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=1/2) to give 126 mg (yield: 60.0%) 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: ethyl acetate-hexane=1/2)

Sources & evidence

ORD record
ord-9f7d9addfa154b0db9790904253ee2dc
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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