Acetic Acid → 3-n-Butyl-6-[4-(2-hydroxyethyl)aminophenyl]uracil

HRID 47970

반응식

HRID 47970 반응식
Cl[C:2]1[NH:7][C:6](=[O:8])[N:5]([CH2:9][CH2:10][CH2:11][CH3:12])[C:4](=[O:13])[CH:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18](CCO)=[CH:17][CH:16]=1.C(N(C(C)C)C(C)C)C.[C:33](O)(=[O:35])[CH3:34]>O>[CH2:9]([N:5]1[C:4](=[O:13])[CH:3]=[C:2]([C:18]2[CH:17]=[CH:16][C:15]([NH:14][CH2:34][CH2:33][OH:35])=[CH:20][CH:19]=2)[NH:7][C:6]1=[O:8])[CH2:10][CH2:11][CH3:12]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 669044-Aminophenethyl alcoholHCID 81531DiisopropylethylamineHCID 141001713-butyl-6-chloropyrimidine-2,4(1H,3H)-dione

생성물 1

HCID 226725173-n-Butyl-6-[4-(2-hydroxyethyl)aminophenyl]uracil

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 6-chloro-3-n-butyluracil (10.4 g, 51.3 mmol), 2-(4-aminophenyl)ethanol (10.0 g, 72.9 mmol) and ethyldiisopropylamine (18 ml, 0.1 mol) was heated with stirring under argon on a 150° oil bath for 1 hr 20 min. The mixture was cooled to room temperature, diluted with 50 ml of water, treated with 10 ml of acetic acid and stirred for crystallization overnight. A precipitated solid was filtered, washed with 2% acetic acid, dried on filter and dissolved in 100 ml of hot 96% ethanol. To the solution 100 ml of hot water was added followed by 1.0 g of charcoal. The mixture was filtered hot and crystallized on ice. Yellow solid was collected by filtration and dried in vacuum to yield 10.7 g of 40, mp 207-208° C. 1H NMR (DMSO-d6) δ0.88 (t, 3H, J=7.3 Hz, CH3), 1.25 (m, 2H, CH2), 1.46 (m, 2H, CH2), 2.70 (t, 2H, J=6.8 Hz, CH2), 3.60 (dd, 2H, J=11.8, 6.8 Hz, CH2), 3.68 (t, 2H, J=7.3 Hz, CH2), 4.62 (t, 1H, J=5.3 Hz, OH), 4.73 (d, 1H, J=1.8 Hz, 5-H), 7.10 (d, 2H, J=8.4 Hz, ArH), 7.23 (d, 2H, J=8.4 Hz, ArH), 7.10 (s, 1H, NH), 10.37 (s, 1H, NH).

후처리

  1. temperaturewas heated
  2. stirringstirred for crystallization overnight
  3. filtrationA precipitated solid was filtered
  4. washwashed with 2% acetic acid
  5. customdried
  6. filtrationon filter
  7. dissolutiondissolved in 100 ml of hot 96% ethanol
  8. additionTo the solution 100 ml of hot water was added
  9. filtrationThe mixture was filtered hot
  10. customcrystallized on ice
  11. filtrationYellow solid was collected by filtration
  12. customdried in vacuum

출처 및 근거

ORD 기록
ord-1a7cd3c3748e4adba57b3e8f5969d752
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699975B2

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