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

HRID 481184Notes

Reaction equation

HRID 481184 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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-d5) 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).

Workup

  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

Sources & evidence

ORD record
ord-efaeb82dff7c4107acad604dfa9727dd
Source dataset
uspto-grants-2003_11
Patent number
US06653473B2

Reaction notes

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