1-Amino-3-[4-cyano-3-methoxyphenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione → 1-Amino-3-[4-cyano-3-hydroxyphenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 430921Notes

Reaction equation

HRID 430921 reaction equation
[NH2:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[C:15]([O:21]C)[CH:14]=2)[C:3]1=[O:23].Cl.[NH+]1C=CC=CC=1>C(O)CCC>[NH2:1][N:2]1[C:7]([C:8]([F:10])([F:9])[F:11])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[C:15]([OH:21])[CH:14]=2)[C:3]1=[O:23]

Participants

4

Reactant 2

HCID 187623381-Amino-3-[4-cyano-3-methoxyphenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dioneHCID 21584435Pyridinium hydrochloride

Product 1

HCID 187623391-Amino-3-[4-cyano-3-hydroxyphenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dioneYield 20.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1-Amino-3-[4-cyano-3-methoxyphenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (2.0 g) and pyridinium hydrochloride (2.1 g) were stirred for 2 hours at 200-210° C. After cooling, the reaction mixture was dissolved in 100 ml of n-butanol, whereupon the solution was washed three times using in each case 30 ml of water. The organic phase was dried over sodium sulfate and subsequently freed from solvent. After crystallization using 10 ml of diisopropyl ether and chromatographic purification of the crude product (eluent: dichloromethane/ethyl acetate=9:1 to 1:1), 0.4 g of the desired product was obtained. M.p.: >230° C.

Workup

  1. temperatureAfter cooling
  2. washwas washed three times
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customAfter crystallization
  5. custom10 ml of diisopropyl ether and chromatographic purification of the crude product (eluent: dichloromethane/ethyl acetate=9:1 to 1:1)

Sources & evidence

ORD record
ord-acccb7a7ad0c48a0a7761e29eccb70f9
Source dataset
uspto-grants-2003_12
Patent number
US06656884B2

Reaction notes

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