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

HRID 2262760ノート

反応式

HRID 2262760 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9bf8a49fe37047bdb27cf0f73cbbebec
出典データセット
uspto-grants-2010_12
特許番号
US07851492B2

反応ノート

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