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

HRID 527413노트

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HRID 527413 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f0bacf24056c4ac28762ba30a734c8fe
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346801B2

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