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

HRID 1250672노트

반응식

HRID 1250672 반응식
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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-76c9eb527b8c4ec5afbde221d7773635
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06339089B2

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