Allylamine → 2-Allylamino-4-dodecylamino-7-methylthieno[3,2-d]pyrimidine

HRID 1250693Notes

Reaction equation

HRID 1250693 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1.[CH2:25]([NH2:28])[CH:26]=[CH2:27].C(=O)([O-])O.[Na+]>>[CH2:25]([NH:28][C:2]1[N:3]=[C:4]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1)[CH:26]=[CH2:27]

Participants

4

Reactant 3

HCID 7853AllylamineHCID 516892Sodium BicarbonateHCID 183263802-Chloro-4-dodecylamino-7-methylthieno[3,2-d]pyrimidine

Product 1

HCID 183265552-Allylamino-4-dodecylamino-7-methylthieno[3,2-d]pyrimidineYield 44.8%

Procedure

442 mg (1.2 mmol) of 2-chloro-4-dodecylamino-7-methylthieno[3,2-d]pyrimidine and 1.10 g (19.2 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 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 209 mg (yield: 44.8%) 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-b78d7a3e5a164c2ea92562478c212581
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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