Allylamine → HCID 15908149, compound

HRID 1250687Notes

Reaction equation

HRID 1250687 reaction equation
[CH2:1]([NH:4][C:5]1[C:6]2[S:14][CH:13]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:7]=2[N:8]=[C:9](Cl)[N:10]=1)[CH:2]=[CH2:3].[CH2:21]([NH2:24])[CH:22]=[CH2:23].C(=O)([O-])O.[Na+]>>[CH2:21]([NH:24][C:9]1[N:10]=[C:5]([NH:4][CH2:1][CH:2]=[CH2:3])[C:6]2[S:14][CH:13]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:7]=2[N:8]=1)[CH:22]=[CH2:23]

Participants

4

Reactant 3

HCID 7853AllylamineHCID 516892Sodium BicarbonateHCID 15908148HCID 15908148, compound

Product 1

HCID 15908149HCID 15908149, compoundYield 85.3%

Procedure

168 mg (0.56 mmol) of 4-allylamino-2-chloro-7-phenylthieno[3,2-d]pyrimidine and 508 mg (8.9 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 (30 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 silica gel chromatography (eluent: ethyl acetate-hexane=1/4) to give 154 mg (yield: 85.3%) of the title compound.

Workup

  1. customAfter completion of the reaction
  2. customto resume room temperature
  3. extractionextraction with ethyl acetate (30 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 silica gel chromatography (eluent: ethyl acetate-hexane=1/4)

Sources & evidence

ORD record
ord-c0edfb31de8f43d7b24af86812b0d245
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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