Allylamine → 2-Allylamino-4-(trans-cinnamylamino)-7-methylthieno[3,2-d]pyrimidine

HRID 1250672Notes

Reaction equation

HRID 1250672 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:12][CH2:13]/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1.[CH2:22]([NH2:25])[CH:23]=[CH2:24].C(=O)([O-])O.[Na+]>>[CH2:22]([NH:25][C:2]1[N:3]=[C:4]([NH:12][CH2:13]/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1)[CH:23]=[CH2:24]

Participants

4

Reactant 3

HCID 7853AllylamineHCID 516892Sodium BicarbonateHCID 183264422-Chloro-4-(trans-cinnamylamino)-7-methylthieno[3,2-d]pyrimidine

Product 1

HCID 183264752-Allylamino-4-(trans-cinnamylamino)-7-methylthieno[3,2-d]pyrimidineYield 81.5%

Procedure

316 mg (1.0 mmol) of 2-chloro-4-(trans-cinnamylamino)-7-methylthieno[3,2-d]pyrimidine and 914 mg (16.0 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=1/4) to give 274 mg (yield: 81.5%) 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-76c9eb527b8c4ec5afbde221d7773635
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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