Potassium Carbonate → 3-[5-(6-Chloropurin-9-yl)pentyloxy]benzamide

HRID 429166노트

반응식

HRID 429166 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH2:13])=[O:12].[Cl:17][C:18]1[N:26]=[CH:25][N:24]=[C:23]2[C:19]=1[NH:20][CH:21]=[N:22]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:17][C:18]1[N:26]=[CH:25][N:24]=[C:23]2[C:19]=1[N:20]=[CH:21][N:22]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH2:13])=[O:12]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 53592776-ChloropurineHCID 183546093-(Bromopentyloxy)benzamide

생성물 1

HCID 183546243-[5-(6-Chloropurin-9-yl)pentyloxy]benzamide수율 20%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 3-(bromopentyloxy)benzamide (500 mg, 1.7 mmols), 6-chloropurine (270 mg, 1.7 mmols) and potassium carbonate (240 mg, 1.7 mmols) in DMF (7.5 ml) was stirred for two days at room temperature. The solvent was then removed under vacuum (0.001 mmHg) and the white solid (mixture of N7 and N9 isomers) was chromatographed (silica, 10% MeOH/CH2CI2) to give a single product (N9 isomer) as a glass. This was triturated with ether (=5 ml) to give a white solid which was recrystallised from ethyl acetate to give the product (120 mg, 0.33 mmols, 20% yield)

후처리

  1. customThe solvent was then removed under vacuum (0.001 mmHg)
  2. additionthe white solid (mixture of N7 and N9 isomers)
  3. customwas chromatographed (silica, 10% MeOH/CH2CI2)
  4. customto give a single product (N9 isomer) as a glass
  5. customThis was triturated with ether (=5 ml)
  6. customto give a white solid which
  7. customwas recrystallised from ethyl acetate

출처 및 근거

ORD 기록
ord-15a0c93450dd4202869c724eba9dcd1b
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316455B1

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