Dimethylformamide → 2-Chloro-9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-9H-purine

HRID 1876622Notes

Reaction equation

CN(C)C=O.[Cl:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][NH:13]2)=[C:9]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]2[CH3:22])[N:8]=1.I[CH2:24][CH:25]([CH3:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[Cl:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[CH2:24][CH:25]([CH3:27])[CH3:26])=[C:9]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]2[CH3:22])[N:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

An N,N-dimethylformamide (5 ml) suspension of 2-chloro-6-((S)-3-methylmorpholin-4-yl)-9H-purine (839 mg, 3.31 mmol), 1-iodo-2-methylpropane (730 mg, 3.97 mmol), and potassium carbonate (594 mg, 4.30 mmol) was stirred at 50° C. for 4 hours. The reaction mixture was returned to room temperature. Ethyl acetate was added to the reaction mixture and the resulting mixture was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and, after filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (hexane:ethyl acetate=7:3) to give the title compound (868 mg, 85%) as an amorphous substance.

Workup

customwas returned to room temperature
washthe resulting mixture was washed with water and saturated brine
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationafter filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by flash silica gel column chromatography (hexane:ethyl acetate=7:3)

Sources & evidence

ORD record: ord-a293d4eb90f54b41948acebb1fa66425
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309546B2

Reaction notes

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