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

HRID 277353

Reaction equation

HRID 277353 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].N12CCCN=C1CCCCC2.CN(C)[C:18]1[O:19][C:20](=[O:28])[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[N:23]=1>C1(C)C(C)=CC=CC=1>[CH:1]([N:4]1[C:20](=[O:28])[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[NH:23][C:18]1=[O:19])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-one

Product 1

HCID 112068123-isopropyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedioneYield 54%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Isopropylamine (1.2 g, 20.3 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU, 6 mL) are added to a solution of 2-dimethylamino-4-trifluoromethyl-6H-1,3-oxazin-6-one (4.0 g, 19.2 mmol) in xylene (34 mL). The resultant reaction mixture is held at 100° C. for 3 hours, cooled, washed with 5 wt. % HCl (40 mL), and extracted with ethyl acetate. The combined organic extracts are concentrated and triturated with heptane. The solids are filtered and dried to give the title product as a yellow powder (2.3 g, 54% yield, mp 127°-129° C.) which is identified by 1H NMR (DMSO-d6) δ6.11 (1H, s), 4.96 (1H, sp), 1.35 (6H, d); and 19F NMR δ−68.9 (s).

Workup

  1. customThe resultant reaction mixture
  2. temperaturecooled
  3. washwashed with 5 wt. % HCl (40 mL)
  4. extractionextracted with ethyl acetate
  5. concentrationThe combined organic extracts are concentrated
  6. customtriturated with heptane
  7. filtrationThe solids are filtered
  8. customdried

Sources & evidence

ORD record
ord-d1f2986d2ff44b47bd6a20692eb54ba4
Source dataset
uspto-grants-2002_03
Patent number
US06355796B1

Linked notes

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