Urea → HCID 135876054, compound

HRID 2189173Notes

Reaction equation

HRID 2189173 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)/[CH:9]=[CH:10]/[C:11]2[S:15][CH:14]=[N:13][C:12]=2[CH3:16])=[CH:4][C:3]=1[CH3:18].[NH2:19][C:20]([NH2:22])=[O:21]>Cl.O1CCOCC1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:11]3[S:15][CH:14]=[N:13][C:12]=3[CH3:16])[NH:22][C:20](=[O:21])[N:19]=2)=[CH:4][C:3]=1[CH3:18]

Participants

5

Reactant 2

HCID 1176UreaHCID 59363804HCID 59363804, compound

Product 1

HCID 135876054HCID 135876054, compoundYield 3.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

(((E)-1-(4-hydroxy-3-methylphenyl)-3-(4-methylthiazol-5-yl)prop-2-en-1-one (200 mg, 0.77 mmol) and urea (0.23 g, 3.8 mmol) were suspended in 5 mL of 4N HCl solution in dioxane (Aldrich), and the reaction mixture was heated in a sealed vessel to 120° C. for 20 h. After cooling to room temperature, the resulting mixture was concentrated in vacuo to remove dioxane. The residue was dissolved in 5 mL of methanol, and the product was purified by preparative HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid) to yield 7.7 mg of 4-(4-hydroxy-3-methylphenyl)-6-(4-methyl-1,3-thiazol-5-yl)pyrimidin-2(1H)-one. 1H NMR (400 MHz, d6-DMSO): δ 9.11 (s, 1H), 7.81 (d, 1H), 7.72 (dd, 1H), 7.07 (s, 1H), 6.90 (d, 1H), 2.73 (s, 3H), 2.17 (s, 3H). MS (EI) for C15H13N3O2S: 300.4 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. customto remove dioxane
  4. dissolutionThe residue was dissolved in 5 mL of methanol
  5. customthe product was purified by preparative HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid)

Sources & evidence

ORD record
ord-f9774a87f98f4c08a010046c47e6f47a
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

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