Hydrochloric Acid → HCID 136348330, compound

HRID 884636Notes

Reaction equation

HRID 884636 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH3:18])[CH:12]=2)=[C:4]([CH3:20])[CH:3]=1.Cl.[NH2:22][C:23]([NH2:25])=[O:24]>CCO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:25][C:23](=[O:24])[N:22]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH3:18])[CH:12]=3)[CH:9]=2)=[C:4]([CH3:20])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1176Urea2×HCID 68599201HCID 68599201, compound

Product 1

HCID 136348330HCID 136348330, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

To a sealed pressure vessel was added (E)-1-(4-amino-2-methylphenyl)-3-(4-hydroxy-3-methylphenyl)prop-2-en-1-one (2) (1.5 g, 5.6 mmol), EtOH (10 mL), 4N HCl in dioxanes (20 mL, 80 mmol), and urea (1.74 g, 29.1 mmol). The pressure vessel was sealed and heated to 110° C. overnight. Another 1 g of urea was added and heated for another 5 h. The reaction was then cooled to rt, concentrated via rotary evaporation and columned purified on silica gel (10:90 to 20:80 MeOH:EtOAc) to give 6-(4-amino-2-methylphenyl)-4-(4-hydroxy-3-methylphenyl)pyrimidin-2(1H)-one (3) (1.1 g, 64% yield).

Workup

  1. customThe pressure vessel was sealed
  2. temperatureheated for another 5 h
  3. temperatureThe reaction was then cooled to rt
  4. concentrationconcentrated via rotary evaporation
  5. customcolumned purified on silica gel (10:90 to 20:80 MeOH:EtOAc)

Sources & evidence

ORD record
ord-01c44c7e1aae4759bf1841fd18cf3ab0
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

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