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

HRID 655813Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 60 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-9911335b916e4de18a120c0a461d91cf
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071609B2

Reaction notes

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