Water → 2,6-Dioxo-5-[3-(3-trifluoromethyl-phenyl)-ureido]-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid

HRID 2262760노트

반응식

HRID 2262760 반응식
[NH2:1][C:2]1[C:10](=[O:11])[NH:9][C:8](=[O:12])[NH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:13][C:14]([F:25])([F:24])[C:15]1[CH:16]=[C:17]([N:21]=[C:22]=[O:23])[CH:18]=[CH:19][CH:20]=1.O>CS(C)=O>[O:12]=[C:8]1[NH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:1][C:22]([NH:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:13])([F:24])[F:25])[CH:16]=2)=[O:23])[C:10](=[O:11])[NH:9]1

참가 물질

5

반응물 3

HCID 962WaterHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 730185-Amino-1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid

생성물 1

HCID 111991292,6-Dioxo-5-[3-(3-trifluoromethyl-phenyl)-ureido]-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

5-Amino-orotic acid (0.86 g) was dissolved in DMSO (10 ml), treated with 3-trifluoromethylphenylisocyanate (0.9 ml) and after an hour with another 0.5 ml. The reaction was stirred for three days at room temperature. Water was added and the mixture was filtered and washed with water. The residue was slurried in water, treated with NaOH and worked through until basic. Filtration and acidification of the filtrate provided a precipitate, which was filtered, washed with water and dried. Recrystallisation from 96% EtOH provided 2,6-dioxo-5-[3-(3-trifluoromethyl-phenyl)-ureido]-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid (330 mg). Mp. >300° C.

후처리

  1. filtrationthe mixture was filtered
  2. washwashed with water
  3. additiontreated with NaOH
  4. filtrationFiltration and acidification of the filtrate
  5. customprovided a precipitate, which
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried
  9. customRecrystallisation from 96% EtOH

출처 및 근거

ORD 기록
ord-9bf8a49fe37047bdb27cf0f73cbbebec
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851492B2

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