Allylamine → HCID 15908144, compound

HRID 1250683Notes

Reaction equation

HRID 1250683 reaction equation
[CH2:1]([NH:4][C:5]1[C:6]2[S:14][CH:13]=[C:12]([CH:15]([CH3:17])[CH3:16])[C:7]=2[N:8]=[C:9](Cl)[N:10]=1)[CH:2]=[CH2:3].[CH2:18]([NH2:21])[CH:19]=[CH2:20].C(=O)([O-])O.[Na+]>>[CH2:18]([NH:21][C:9]1[N:10]=[C:5]([NH:4][CH2:1][CH:2]=[CH2:3])[C:6]2[S:14][CH:13]=[C:12]([CH:15]([CH3:17])[CH3:16])[C:7]=2[N:8]=1)[CH:19]=[CH2:20]

Participants

4

Reactant 3

HCID 7853AllylamineHCID 516892Sodium BicarbonateHCID 15908143HCID 15908143, compound

Product 1

HCID 15908144HCID 15908144, compoundYield 89.3%

Procedure

70 mg (0.26 mmol) of 4-allylamino-2-chloro-7-isopropylthieno[3,2-d]pyrimidine and 239 mg (4.2 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 67 mg (yield: 89.3%) 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-c4d69a6e42fb450080a060727a3f50ff
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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