Allylamine → HCID 18326489, compound

HRID 1250666Notes

Reaction equation

HRID 1250666 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:12][CH2:13][C:14]#[CH:15])[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1.[CH2:16]([NH2:19])[CH:17]=[CH2:18].C(=O)([O-])O.[Na+]>>[CH2:16]([NH:19][C:2]1[N:3]=[C:4]([NH:12][CH2:13][C:14]#[CH:15])[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1)[CH:17]=[CH2:18]

Participants

4

Reactant 3

HCID 7853AllylamineHCID 516892Sodium BicarbonateHCID 18326408HCID 18326408, compound

Product 1

HCID 18326489HCID 18326489, compoundYield 54.2%

Procedure

285 mg (1.2 mmol) of 2-chloro-7-methyl-4-(2-propynylamino)thieno[3,2-d]pyrimidine and 1.14 mg (19.2 mmol) of allylamine 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=1/2) to give 168 mg (yield: 54.2%) 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=1/2)

Sources & evidence

ORD record
ord-b9301310826f4d429ee1b9f2cd3c7c15
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

Loading…