HCID 57343536、化合物 → Tert-butyl (3-((5-formyl-2-(methylthio)pyrimidin-4-yl)amino)phenyl)carbamate

HRID 527394ノート

反応式

HRID 527394 の反応式
[OH:1][CH2:2][C:3]1[C:4]([NH:11][C:12]2[CH:13]=[C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:15]=[CH:16][CH:17]=2)=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[C:21]([O:20][C:19](=[O:25])[NH:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([NH:11][C:4]2[C:3]([CH:2]=[O:1])=[CH:8][N:7]=[C:6]([S:9][CH3:10])[N:5]=2)[CH:13]=1)([CH3:24])([CH3:23])[CH3:22]

参加物

4

反応物 1

HCID 57343536HCID 57343536、化合物

生成物 1

HCID 57343702Tert-butyl (3-((5-formyl-2-(methylthio)pyrimidin-4-yl)amino)phenyl)carbamate収率 43%

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 6212Chloroform溶媒

実験手順

At RT, manganese (IV) oxide (358 g, 4.1 mol) was added to a solution of tert-butyl (3-((5-(hydroxymethyl)-2-(methylthio)pyrimidin-4-yl)amino)phenyl)carbamate (50d) (140 g, 386.8 mmol) in CHCl3. After 18 h, the reaction mixture was filtered through a pad of Celite washing with 3×100 mL of CHCl3. The filtrate was concentrated and the residue was purified on a silica gel column (eluted with 15-65% EtOAc in hexanes) to give tert-butyl(3-((5-formyl-2-(methylthio)pyrimidin-4-yl)amino)phenyl)carbamate (60 g, 43% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 10.61 (1H, br. s.), 9.77 (1H, s), 8.44 (1H, s), 7.99 (1H, br. s.), 7.33-7.39 (1H, m), 7.27-7.30 (1H, m), 7.00-7.06 (1H, m), 6.41-6.55 (1H, m), 2.59 (3H, s), 1.53 (9H, s). m/z (ESI, +ve ion) 361.1 (M+1)+.

後処理

  1. filtrationthe reaction mixture was filtered through a pad of Celite
  2. washwashing with 3×100 mL of CHCl3
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified on a silica gel column (eluted with 15-65% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-fcd48ca84f914680981a3fc7111e9fbf
出典データセット
uspto-grants-2016_05
特許番号
US09346801B2

反応ノート

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