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Isopropyl iodide → N-(4-(Dimethylphosphoryl)phenyl)-2-isopropyl-9-vinyl-9H-purin-6-amine

HRID 2041928
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HRID 2041928 반응식
[CH:1](I)([CH3:3])[CH3:2].[CH3:5][P:6]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:24]=[C:23](I)[N:22]=[C:21]3[C:17]=2[N:18]=[CH:19][N:20]3[CH:26]=[CH2:27])=[CH:11][CH:10]=1)([CH3:8])=[O:7].[I-].C([Zn+])(C)C.C1COCC1>CN(C=O)C.[Zn].C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:5][P:6]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:24]=[C:23]([CH:1]([CH3:3])[CH3:2])[N:22]=[C:21]3[C:17]=2[N:18]=[CH:19][N:20]3[CH:26]=[CH2:27])=[CH:11][CH:10]=1)([CH3:8])=[O:7]
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참가 물질

7

반응물 3

HCID 6362Isopropyl iodideHCID 86631263N-(4-(dimethylphosphoryl)phenyl)-2-iodo-9-vinyl-9H-purin-6-amineHCID 178420666HCID 178420666, 화합물

생성물 1

HCID 68926097N-(4-(Dimethylphosphoryl)phenyl)-2-isopropyl-9-vinyl-9H-purin-6-amine

시약·촉매·용매 3

HCID 70451953Zinc THF촉매
HCID 178418476
HCID 178418476, 화합물
촉매
HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

In a dry Argon atmosphere Reike Zinc/THF suspension (5 g/100 mL) (2.54 mL, 2.0 mmol) was transferred into a round-bottom flask via syringe with a 12 gauge needle. Then isopropyl iodide (0.18 mL, 1.82 mmol) was added and stirring was started right away. The content turned warm and stirring was continued at rt for 4-5 hours. In a 10 mL CEM microwave tube was dissolved N-(4-(dimethylphosphoryl)phenyl)-2-iodo-9-vinyl-9H-purin-6-amine (0.20 g, 0.46 mmol), PdCl2(PPh3)2 (19 mg, 0.027 mmol) in 1 mL dry DMF. Isopropylzinc iodide/THF solution was transferred to the microwave tube via syringe. The reaction was heated on microwave (60° C./5 min). The reaction mixture was filtered through celite, washed with EtOAc, the filtrate was concentrated, purified on ISCO combiFlash Column (SiO2, 12 g).

후처리

  1. temperatureThe content turned warm
  2. stirringstirring
  3. filtrationThe reaction mixture was filtered through celite
  4. washwashed with EtOAc
  5. concentrationthe filtrate was concentrated
  6. custompurified on ISCO combiFlash Column (SiO2, 12 g)

출처 및 근거

ORD 기록
ord-c288d0a888e643ed8a2cd843316fd7f9
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08586566B2

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