Potassium Carbonate → N2-Butyl-8-(methoxy)-9-(tetrahydro-3-furanylmethyl)-9H-Purine-2,6-diamine

HRID 1011053Notes

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+].CS(O[CH2:36][CH:37]1[CH2:41][CH2:40][O:39][CH2:38]1)(=O)=O.ClC1N=C2C(N=CN2CC2CCOCC2)=C(Cl)N=1>CN(C)C=O.C(OCC)(=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[CH2:36][CH:37]2[CH2:41][CH2:40][O:39][CH2:38]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N2-butyl-8-methoxy-9H-purine-2,6-diamine trifluoroacetic acid salt (4.60 g) in dry N,N-dimethylformamide (55 ml) at room temperature and under was added potassium carbonate (7.25 g) in one go. The reaction was heated to 60° C. for 1.5 hours. A solution of tetrahydro-3-furanylmethyl methanesulfonate, Isomer 2 (2.6 g) in dry N,N-dimethylformamide (3 ml) was added via a Pasteur pipette and the reaction heated at 70° C. for 16 hours. The reaction was cooled to room temperature, diluted with ethyl acetate (100 ml) and washed with brine (20 ml). The organic layer was concentrated in vacuo. The product was purified by C18 reverse phase chromatography using water (0.1% formic acid)-acetonitrile (0.05% formic acid) as eluant (10-60%) to afford the title compound as a clear viscous oil (3 g).

Workup

temperaturethe reaction heated at 70° C. for 16 hours
temperatureThe reaction was cooled to room temperature
washwashed with brine (20 ml)
concentrationThe organic layer was concentrated in vacuo
customThe product was purified by C18 reverse phase chromatography

Sources & evidence

ORD record: ord-1a637a32dbec4729852269de4ac157ba
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977344B2

Reaction notes

Loading…