Sodium Carbonate → tert-butyl (3-(6-ethyl-2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate

HRID 527413ノート

反応式

HRID 527413 の反応式
[CH2:1]([C:3]1[C:14](=[O:15])[N:13]([C:16]2[CH:17]=[C:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:20][CH:21]=2)[C:6]2[N:7]=[C:8]([S:11][CH3:12])[N:9]=[CH:10][C:5]=2[CH:4]=1)[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:35].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([C:3]1[C:14](=[O:15])[N:13]([C:16]2[CH:17]=[C:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:20][CH:21]=2)[C:6]2[N:7]=[C:8]([S:11]([CH3:12])=[O:35])[N:9]=[CH:10][C:5]=2[CH:4]=1)[CH3:2]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 86732011tert-butyl (3-(6-ethyl-2-(methylthio)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate

生成物 1

HCID 86732026tert-butyl (3-(6-ethyl-2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate収率 91%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

At 0° C., a suspension of tert-butyl (3-(6-ethyl-2-(methylthio)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate (55) (720 mg, 1.75 mmol) in DCM (15 mL) was treated with 3-chloroperoxybenzoic acid (70 wt. %, 460 mg, 1.87 mmol) in one portion and stirred at 0° C. for 1 h. The reaction mixture was diluted with DCM (15 mL), and treated with ice and a 10% solution of Na2CO3 (ca. 10 mL). The DCM layer was separated and the aqueous layer was extracted with an additional amount of DCM (2×50 mL), dried over sodium sulfate and concentrated to give tert-butyl (3-(6-ethyl-2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate (6a) (682 mg, 1.59 mmol, 91% yield) as a light yellow amorphous solid. m/z (ESI, +ve ion) 451.0 (M+Na)+. The crude material was used in the subsequent step without further purification.

後処理

  1. additiontreated with ice
  2. customThe DCM layer was separated
  3. extractionthe aqueous layer was extracted with an additional amount of DCM (2×50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-f0bacf24056c4ac28762ba30a734c8fe
出典データセット
uspto-grants-2016_05
特許番号
US09346801B2

反応ノート

読み込み中…