Dimethylformamide → 4-chloro-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

HRID 1011299노트

반응식

HRID 1011299 반응식
[CH2:1]([O:3][C:4]([C:6]1[NH:15][C:9]2[N:10]=[CH:11][N:12]=[C:13]([Cl:14])[C:8]=2[CH:7]=1)=[O:5])[CH3:2].CN(C=O)C.[H-].[Na+].[CH3:23][Si:24]([CH2:27][CH2:28][O:29][CH2:30]Cl)([CH3:26])[CH3:25]>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:15]([CH2:30][O:29][CH2:28][CH2:27][Si:24]([CH3:26])([CH3:25])[CH3:23])[C:9]2[N:10]=[CH:11][N:12]=[C:13]([Cl:14])[C:8]=2[CH:7]=1)=[O:5])[CH3:2]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 21262606Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate

생성물 1

HCID 589380134-chloro-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid ethyl ester수율 84%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a round bottom flask equipped with a magnetic stir bar was added 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.13 g, 0.58 mmol, 1.0 eq.) and DMF (3 ml). The mixture was cooled to 0° C. followed by the addition of NaH (0.028 g, 0.70 mmol, 1.2 eq) with stirring. After stirring for 10 minutes SEM-CL (0.106 g, 0.64 mmol, 1.1 eq) was added and the reaction was allowed to warm to room temperature with stirring for 1 hour. The reaction was diluted with ethyl acetate (50 ml), washed (2×) water, (1×) NaHCO3, (2×) 5% LiCl, (1×) brine, and dried over sodium sulfate, and concentrated in vacuo to give 4-chloro-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid ethyl ester as a cream solid (0.17 g, 84%). MS (ESI) for C15H22ClN3O3Si: 356 (MH+).

후처리

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. additionwas added
  3. temperatureto warm to room temperature
  4. stirringwith stirring for 1 hour
  5. washwashed (2×) water, (1×) NaHCO3, (2×) 5% LiCl, (1×) brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-79f6742dd0e64bcb9a0abfa899927570
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977345B2

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