Allyl bromide → 4-(9-allyl-2-chloro-8-iodo-9H-purin-6-yl)morpholine

HRID 334123Notes

Reaction equation

[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([I:11])[NH:8]2)=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:24](Br)[CH:25]=[CH2:26]>CN(C=O)C.[Cl-].[Na+].O.C(Cl)Cl>[CH2:26]([N:8]1[C:7]([I:11])=[N:6][C:5]2[C:9]1=[N:10][C:2]([Cl:1])=[N:3][C:4]=2[N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)[CH:25]=[CH2:24]

Participants

Conditions

Temperature: 50 °C

Procedure

4-(2-chloro-8-iodo-9H-purin-6-yl)morpholine (500 mg, 1.0 mmol) was stirred together with cesium carbonate (890 mg, 2.7 mmol) in DMF (4.2 mL) at ambient temperature for 10 minutes. Allyl bromide (0.36 mL, 4.1 mmol) was introduced and the reaction mixture was heated at 50° C. for 2 hr. The mixture was cooled to ambient temperature and diluted with brine and DCM and the layers separated. The aqueous phase was extracted into DCM (3×), dried over sodium sulfate, filtered, and absorbed onto celite for purification by flash chromatography to afford 4-(9-allyl-2-chloro-8-iodo-9H-purin-6-yl)morpholine as a white foam (480 mg, 90%). 1H NMR (500 MHz, DMSO) δ 5.94 (d, J=10.6 Hz, 2H), 5.76 (s, 1H), 5.19 (d, J=10.3 Hz, 2H), 4.79 (d, J=16.9 Hz, 2H), 4.69 (s, 2H), 3.73 (s, 4H). LC/MS (ESI+): m/z 406 (M+H)

Workup

temperatureThe mixture was cooled to ambient temperature
customthe layers separated
extractionThe aqueous phase was extracted into DCM (3×)
dry with materialdried over sodium sulfate
filtrationfiltered
customabsorbed onto celite for purification by flash chromatography

Sources & evidence

ORD record: ord-9b834834cb5941808a64b789205b8fbf
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883799B2

Reaction notes

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