2-Methoxyethylamine → HCID 18326387, compound

HRID 1250650Notes

Reaction equation

HRID 1250650 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].[CH3:16][O:17][CH2:18][CH2:19][NH2:20].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:20][CH2:19][CH2:18][O:17][CH3:16])[N:10]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 80182-MethoxyethylamineHCID 516892Sodium BicarbonateHCID 18326500HCID 18326500, compound

Product 1

HCID 18326387HCID 18326387, compoundYield 82.3%

Procedure

287 mg (1.2 mmol) of 4-allylamino-2-chloro-7-methylthieno[3,2-d]pyrimidine and 1.44 mg (19.2 mmol) of 2-methoxyethylamine 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 silica gel chromatography (eluent: ethyl acetate-hexane=1/4) to give 274 mg (yield: 82.3%) 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 silica gel chromatography (eluent: ethyl acetate-hexane=1/4)

Sources & evidence

ORD record
ord-b3eabb6e6c2a4590a5aaf8dd9a1c73fc
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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