1-Bromo-3-chloropropane → N2-Butyl-9-(3-chloropropyl)-8-(methyloxy)-9H-purine-2,6-diamine

HRID 2038178Notes

Reaction equation

FC(F)(F)C(O)=O.[CH2:8]([NH:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH2:34][Cl:35]>CN(C=O)C>[CH2:8]([NH:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:32][CH2:33][CH2:34][Cl:35])=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Participants

Conditions

Temperature: 50 °C

Procedure

N2-Butyl-8-(methyloxy)-9H-purine-2,6-diamine trifluoroacetic acid salt (for example, as prepared for Intermediate 8) (701 mg, 2.001 mmol) and potassium carbonate (690 mg, 4.99 mmol) were suspended in DMF (10 mL) and the mixture heated at 50° C. under nitrogen for 2 hours. The mixture was allowed to cool and then 1-bromo-3-chloropropane (198 μL, 2.002 mmol) was added and the reaction mixture stirred at ambient temperature overnight. After 16 hours the reaction mixture was partitioned between water and DCM (25 mL of each). The aqueous phase was extracted with further DCM (2×20 mL). The combined DCM extracts were dried over magnesium sulphate and concentrated in vacuo to give the impure title compound as a pale yellow oil with some solid present (0.76 g) which was used without further purification.

Workup

temperatureto cool
customAfter 16 hours the reaction mixture was partitioned between water and DCM (25 mL of each)
extractionThe aqueous phase was extracted with further DCM (2×20 mL)
dry with materialThe combined DCM extracts were dried over magnesium sulphate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-840dccacd09746db9577b8e7b2cc3bfa
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575340B2

Reaction notes

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