Triethylamine → (S)-9-(5-chloropentyl)-8-methoxy-2-(pentan-2-yloxy)-9H-purin-6-amine

HRID 590430Notes

Reaction equation

FC(F)(F)C(O)=O.[CH3:8][C@H:9]([O:13][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[C:19]([O:23][CH3:24])[NH:20]2)=[C:16]([NH2:25])[N:15]=1)[CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][Cl:38].C(N(CC)CC)C>CN(C=O)C.O.[Cl-].[Na+].O>[Cl:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][N:20]1[C:19]([O:23][CH3:24])=[N:18][C:17]2[C:21]1=[N:22][C:14]([O:13][C@@H:9]([CH3:8])[CH2:10][CH2:11][CH3:12])=[N:15][C:16]=2[NH2:25]

Participants

Conditions

Temperature: 20 °C

Procedure

2-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9H-purin-6-amine trifluoroacetate (600 mg, 1.642 mmol) and potassium carbonate (567 mg, 4.11 mmol) were stirred at 60° C. in DMF (10 ml) for 1 hour under nitrogen. The reaction was cooled to room temperature when 1-bromo-5-chloropentane (0.216 ml, 1.642 mmol) and triethylamine (0.343 ml, 2.464 mmol) were added and the mixture stirred at 20° C. under nitrogen for 16 hours. The mixture was then diluted with water (10 ml) and brine (10 ml) and extracted with DCM (2×10 ml). The combined organic extracts were evaporated and the residue dissolved in DCM and purified by column chromatography using the Flashmaster II (70 g aminopropyl cartridge) with a 0-100% ethyl acetate in cyclohexane gradient over 40 mins. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a yellow gum (430 mg).

Workup

additionwere added
extractionextracted with DCM (2×10 ml)
customThe combined organic extracts were evaporated
dissolutionthe residue dissolved in DCM
custompurified by column chromatography
customover 40 mins
customevaporated in vacuo

Sources & evidence

ORD record: ord-5fafc587bdc04a25a0035c2b722fea33
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233962B2

Reaction notes

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