Triethylamine → (5-Chlorothieno[2,3-d]pyrimidin-4-yl)-[1-(4-isopropylphenyl)ethyl]amine

HRID 1678047

반응식

HRID 1678047 반응식
Cl[C:2]1[C:3]2[C:10]([Cl:11])=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH:12]([C:15]1[CH:20]=[CH:19][C:18]([CH:21]([NH2:23])[CH3:22])=[CH:17][CH:16]=1)([CH3:14])[CH3:13].C(N(CC)CC)C>CN(C=O)C.O>[Cl:11][C:10]1[C:3]2[C:2]([NH:23][CH:21]([C:18]3[CH:19]=[CH:20][C:15]([CH:12]([CH3:14])[CH3:13])=[CH:16][CH:17]=3)[CH3:22])=[N:7][CH:6]=[N:5][C:4]=2[S:8][CH:9]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 37280391-(4-Isopropylphenyl)ethanamine2회HCID 157457684,5-Dichlorothieno[2,3-d]pyrimidine

생성물 1

HCID 58629060(5-Chlorothieno[2,3-d]pyrimidin-4-yl)-[1-(4-isopropylphenyl)ethyl]amine수율 87.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4,5-dichlorothieno[2,3-d]pyrimidine (prepared as taught in EP 447,891) (775 mg, 3.8 mmol), 1-(4-isopropylphenyl)ethanamine (compound 95) (734 mg, 4.5 mmol), and triethylamine (767 mg, 7.6 mmol) in DMF (20 mL) was allowed to react for 24 hours at 20° C. The reaction mixture was diluted with water and extracted thrice with Et2O. The organic portions were combined, washed with brine, and dried (Na2SO4). The mixture was filtered through silica gel, and the solvent was removed in vacuo. The residue was purified by flash chromatography (15 percent Et2O in pentane), yielding 1.1 g of oil.

후처리

  1. customto react for 24 hours at 20° C
  2. extractionextracted thrice with Et2O
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationThe mixture was filtered through silica gel
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by flash chromatography (15 percent Et2O in pentane)

출처 및 근거

ORD 기록
ord-0eaed487a385406cba3fe6eaed1b590d
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008487B2

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