Peracetic Acid → tert-butyl (3-(2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate

HRID 527396

反応式

HRID 527396 の反応式
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10](=[O:13])[N:9]([C:14]3[CH:15]=[C:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:17]=[CH:18][CH:19]=3)[C:7]=2[N:8]=1.C(OO)(=[O:30])C.S([O-])([O-])(=O)=S.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][S:2]([C:3]1[N:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10](=[O:13])[N:9]([C:14]3[CH:15]=[C:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])[CH:17]=[CH:18][CH:19]=3)[C:7]=2[N:8]=1)=[O:30]

参加物

6

反応物 4

HCID 6585Peracetic AcidHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 86732006tert-butyl (3-(2-(methylthio)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate

生成物 1

HCID 86732007tert-butyl (3-(2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate収率 104.4%

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-(2-(methylthio)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate (51) (3.57 g, 9.29 mmol) in DCM (80 mL) was treated with peracetic acid (32 wt % in AcOH, 1.95 mL, 9.29 mmol) slowly dropwise. After 5-10 min, the reaction mixture became a homogeneous yellow solution, and after 20 min, it became a suspension again. After 1 h, the reaction mixture was treated with DCM (50 mL) followed by a solution of aqueous sodium thiosulfate and stirred at 0° C. for 5 min. It was then treated with a saturated solution of NaHCO3, extracted with DCM (6×50 mL), dried over MgSO4, filtered and concentrated affording tert-butyl (3-(2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate (52) (2.50 g, 9.70 mmol, 67% yield) as a light yellow crystalline solid. The crude material was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.58 (1H, s), 9.28 (1H, s), 8.18 (1H, d, J=9.6 Hz), 7.53 (1H, s), 7.37-7.47 (2H, m), 6.89-6.95 (2H, m), 2.71 (3H, s), 1.46 (9H, s). m/z (ESI, +ve ion) 422.9 (M+Na)+.

後処理

  1. waitafter 20 min
  2. waitAfter 1 h
  3. extractionextracted with DCM (6×50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-e1f7b14067a74c7da3f7fb934baee6bf
出典データセット
uspto-grants-2016_05
特許番号
US09346801B2

関連ノート

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