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

HRID 1250623Notes

Reaction equation

HRID 1250623 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[CH2:5]([NH:12][C:13]1[C:14]2[S:22][CH:21]=[C:20]([CH3:23])[C:15]=2[N:16]=[C:17](Cl)[N:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O>[CH2:1]([NH:4][C:17]1[N:18]=[C:13]([NH:12][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:14]2[S:22][CH:21]=[C:20]([CH3:23])[C:15]=2[N:16]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 183264544-Benzylamino-2-chloro-7-methylthieno[3,2-d]pyrimidine

Product 1

HCID 183264342-Allylamino-4-benzylamino-7-methylthieno[3,2-d]pyrimidineYield 81.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

In 2.28 g (40.0 mmol) of allylamine was dissolved 250 mg (0.9 mmol) of 4-benzylamino-2-chloro-7-methylthieno[3,2-d]pyrimidine, and the resulting solution was heated in a sealed tube at 140° C. for 24 hours. After the reaction mixture was cooled, 100 ml of water was added thereto, followed by extraction with ethyl acetate (20 ml×3). The organic layer was washed with 20 ml of water and dried over anhydrous sodium sulfate, and then the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent: ethyl acetate-hexane=1/4) to give 217 mg (yield: 81.3%) of the title compound.

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. extractionfollowed by extraction with ethyl acetate (20 ml×3)
  3. washThe organic layer was washed with 20 ml of water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate-hexane=1/4)

Sources & evidence

ORD record
ord-43f2b943b3114253b4617cd006c80fd1
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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