Water → 3-isopropyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

HRID 428383Notes

Reaction equation

HRID 428383 reaction equation
C(O[C:4]([NH:6]/[C:7](/[C:14]([F:17])([F:16])[F:15])=[CH:8]\[C:9]([O:11]CC)=O)=[O:5])C.[CH:18]([NH2:21])([CH3:20])[CH3:19].O>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[CH:18]([N:21]1[C:9](=[O:11])[CH:8]=[C:7]([C:14]([F:15])([F:16])[F:17])[NH:6][C:4]1=[O:5])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 962WaterHCID 6363IsopropylamineHCID 11288292Ethyl 3-[(ethoxycarbonyl)amino]-4,4,4-trifluorocrotonate

Product 1

HCID 112068123-isopropyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedioneYield 61%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of ethyl 3-[(ethoxycarbonyl)amino]-4,4,4-trifluorocrotonate, (Z)-(2.04 g, 8 mmol), isopropylamine (0.567 g, 9.6 mmol), and 1,8-diazabi-cyclo[5,4,0]undec-7-ene (DBU, 1.46 g, 9.6 mmol) in xylene (15 mL) is heated at 100° C. for 3 hours, cooled, and diluted with ethyl acetate. Water is added, and the resultant aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water and aqueous 2 N hydrochloric acid, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to obtain a solid. The solid is crystallized from methanol/water to give the title product as a solid (1.08 g, 61% yield) which is identified by 1H and 19F NMR spectral analyses.

Workup

  1. temperaturecooled
  2. extractionthe resultant aqueous mixture is extracted with ethyl acetate
  3. washwashed sequentially with water and aqueous 2 N hydrochloric acid
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto obtain a solid
  8. customThe solid is crystallized from methanol/water

Sources & evidence

ORD record
ord-d6014b4698e24e72b96638152dfdab76
Source dataset
uspto-grants-2001_11
Patent number
US06313295B1

Reaction notes

Loading…