Isopropanol → 4-tert-butyl-N-[6-{2-(5-(1-hydroxyethyl)pyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide

HRID 1082271ノート

反応式

HRID 1082271 の反応式
[C:1]([C:4]1[CH:5]=[N:6][C:7]([O:10][CH2:11][CH2:12][O:13][C:14]2[N:19]=[CH:18][N:17]=[C:16]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:15]=2[O:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH3:42])[CH:36]=2)=[N:8][CH:9]=1)(=[O:3])[CH3:2].O1CCCC1.C(O)(C)C.[BH4-].[Na+]>O>[C:30]([C:27]1[CH:26]=[CH:25][C:24]([S:21]([NH:20][C:16]2[C:15]([O:34][C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH3:42])[CH:36]=3)=[C:14]([O:13][CH2:12][CH2:11][O:10][C:7]3[N:8]=[CH:9][C:4]([CH:1]([OH:3])[CH3:2])=[CH:5][N:6]=3)[N:19]=[CH:18][N:17]=2)(=[O:23])=[O:22])=[CH:29][CH:28]=1)([CH3:33])([CH3:31])[CH3:32]

参加物

6

反応物 4

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydride2 回HCID 19689514HCID 19689514、化合物

生成物 1

HCID 196894724-tert-butyl-N-[6-{2-(5-(1-hydroxyethyl)pyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide収率 75.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of N-[6-{2-(5-acetylpyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (756 mg), tetrahydrofuran (10 ml) and isopropyl alcohol (10 ml) is added with stirring sodium borohydride (48 mg) under ice-cooling, and the mixture is stirred for 40 minutes under ice-cooling. To the reaction solution is further added sodium borohydride (14 mg), and the mixture is stirred for 30 minutes. The mixture is diluted with water, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and concentrated to dryness under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1~20:1), and recrystallized from ethyl acetate/n-hexane to give 4-tert-butyl-N-[6-{2-(5-(1 -hydroxyethyl)pyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide (571 mg) as crystals.

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture is stirred for 30 minutes
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer is washed
  6. customdried
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1~20:1)
  9. customrecrystallized from ethyl acetate/n-hexane

出典と根拠

ORDレコード
ord-48c503c1218d4790b92446966b6558dd
出典データセット
uspto-grants-1996_12
特許番号
US05589478

反応ノート

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