Sulfuric Acid → 1-Amino-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 1953995

Reaction equation

S(=O)(=O)(O)O.[NH2:6][N:7]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10](=[O:17])[N:9]([C:18]2[CH:23]=[C:22]([O:24]C(C)C)[C:21]([Cl:28])=[CH:20][C:19]=2[F:29])[C:8]1=[O:30]>C(Cl)Cl.O>[NH2:6][N:7]1[C:12]([C:13]([F:14])([F:15])[F:16])=[CH:11][C:10](=[O:17])[N:9]([C:18]2[CH:23]=[C:22]([OH:24])[C:21]([Cl:28])=[CH:20][C:19]=2[F:29])[C:8]1=[O:30]

Participants

Conditions

Temperature: 0 °C

Procedure

Conc. sulfuric acid (3 ml) was added to a solution of 1-amino-3-(4-chloro-2-fluoro-5-isopropyloxyphenyl)-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (4.5 g) in methylene chloride (50 ml) stirred at 0° C. . After 1 hour the mixture was diluted with water and processed. The oily product was chromatographed on silica gel eluting with ethyl acetate:hexane, 2:3, to give 1-amino-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione as a pale yellow amorphous solid (3.6 g,). 1H NMR (CDCl3,TMS): 7.27(1H, d, J=8.8 Hz), 6.88(1H, d, J=6.5 Hz), 6.28(1H, s), 5.86(1H, br. s), 4.61(2H, s)

Workup

customThe oily product was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record: ord-3a54aec8f3674defa24a29fe10fb710f
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121201

Linked notes

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