Hydrochloric Acid → [2-Bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methanol

HRID 1508714ノート

反応式

HRID 1508714 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:17]([CH2:18][CH3:19])=[C:16]([CH3:20])[N:15]=[C:14]([C:21]3[S:22][C:23]([Cl:26])=[CH:24][CH:25]=3)[N:13]=2)=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:17]([CH2:18][CH3:19])=[C:16]([CH3:20])[N:15]=[C:14]([C:21]3[S:22][C:23]([Cl:26])=[CH:24][CH:25]=3)[N:13]=2)=[CH:7][C:3]=1[CH2:4][OH:5]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 901105222-Bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]benzoic acid

生成物 1

HCID 90112603[2-Bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methanol収率 35%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A 100-mL round bottomed flask was charged with 2-bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]benzoic acid (impure, obtained from several reactions on 1.3 mmol scale), THF (20 ml). To the mixture was added BH3 (1N in THF, 7.5 ml). The resulting mixture was stirred at rt overnight. Then treated with 2N HCl aq. (10 ml) followed by sodium bicarbonate to pH=7. The mixture was extracted with ethyl acetate (3×10 ml). The organic layers were combined and dried over Na2SO4. Removal of solvent gave a residue, which was purified by chromatography on silica gel using 0.5% of methanol in dichloromethane to give the title compound (198 mg, 35% yield).

後処理

  1. extractionThe mixture was extracted with ethyl acetate (3×10 ml)
  2. dry with materialdried over Na2SO4
  3. customRemoval of solvent
  4. customgave a residue, which
  5. customwas purified by chromatography on silica gel using 0.5% of methanol in dichloromethane

出典と根拠

ORDレコード
ord-391e18d601754b75986303392d94a40a
出典データセット
uspto-grants-2015_12
特許番号
US09221843B2

反応ノート

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