Water → N-(4-(6-Aminopyrimidin-4-yloxy)phenyl)-N'-(3-methanesulfonylphenyl)urea

HRID 853512ノート

反応式

HRID 853512 の反応式
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH2:13])[CH:8]=2)=[CH:4][CH:3]=1.C1([O:22][C:23](=O)[NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:26]=2)C=CC=CC=1.C(OCC)(=O)C.O>CS(C)=O.CO>[NH2:13][C:9]1[N:10]=[CH:11][N:12]=[C:7]([O:6][C:5]2[CH:14]=[CH:15][C:2]([NH:1][C:23]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:26]=3)=[O:22])=[CH:3][CH:4]=2)[CH:8]=1

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl Acetate2 回HCID 22936234Phenyl 3-methylsulfonylphenylcarbamateHCID 229363746-(4-Amino-phenoxy)-pyrimidin-4-ylamine

生成物 1

HCID 22936323N-(4-(6-Aminopyrimidin-4-yloxy)phenyl)-N'-(3-methanesulfonylphenyl)urea収率 43%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 887Methanol溶媒

実験手順

6-(4-Aminophenoxy)pyrimidin-4-ylamine (88.9 mg, 0.440 mmol) and (3-methylsulfonylphenyl)carbamic acid phenyl ester (128 mg, 0.440 mmol) were stirred in dimethylsulfoxide (2 ml) at 85° C. for18 hours. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with 1N aqueous sodium hydroxide, water and saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent—ethyl acetate:methanol=30:1), the fraction containing the target substance was concentrated and suspended in ethyl acetate, the suspension was diluted with hexane and the crystals were filtered out, washed with hexane and blow-dried to obtain the title compound (75.0 mg, 0.188 mmol, 43%) as colorless crystals.

後処理

  1. washthe organic layer was washed with 1N aqueous sodium hydroxide, water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered off
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe obtained crude product
  6. additionthe fraction containing the target substance
  7. concentrationwas concentrated
  8. additionthe suspension was diluted with hexane
  9. filtrationthe crystals were filtered out
  10. washwashed with hexane
  11. customblow-dried

出典と根拠

ORDレコード
ord-c55124e11c04488dad18f3cc8904bfb3
出典データセット
uspto-grants-2007_08
特許番号
US07253286B2

反応ノート

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