Imidazole → 3-(1H-imidazol-1-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate

HRID 870596노트

반응식

HRID 870596 반응식
[H-].[Na+].[CH2:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]1[NH:12][C:13]1[N:14]=[CH:15][C:16]2[CH2:21][N:20]([C:22]([O:24][CH2:25][CH2:26][CH2:27]Cl)=[O:23])[CH2:19][C:17]=2[N:18]=1.[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1>CN(C)C=O.ClCCl>[CH2:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]1[NH:12][C:13]1[N:14]=[CH:15][C:16]2[CH2:21][N:20]([C:22]([O:24][CH2:25][CH2:26][CH2:27][N:29]3[CH:33]=[CH:32][N:31]=[CH:30]3)=[O:23])[CH2:19][C:17]=2[N:18]=1

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 867265623-Chloropropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate

생성물 1

HCID 867265613-(1H-imidazol-1-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate수율 30%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

Add sodium hydride (0.068 g; 2.25 equiv; 1.70 mmoles) to a solution of: 3-chloropropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate (0.283 g; 1.0 equiv; 0.76 mmoles), and 1H-imidazole (0.105 g; 2.0 equiv; 1.54 mmoles) in dimethylformamide (2.4 mL). Stir the reaction mixture for 16 hours, then dilute with dichloromethane and wash with water. Extract the aqueous layer with dichloromethane twice. Concentrate the combined organic extracts and then purify the crude product by column chromatography (0 to 10% methanol in dichloromethane) to afford of 3-(1H-imidazol-1-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate (0.0922 g; 30%) as a yellow solid: MS (m/z): 405(M+1).

후처리

  1. washwash with water
  2. extractionExtract the aqueous layer with dichloromethane twice
  3. concentrationConcentrate the combined organic extracts
  4. custompurify the crude product by column chromatography (0 to 10% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-3c12fbb077c646fbbf6c09a46dd60329
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969555B2

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