Potassium Carbonate → 2-Butyloxy-8-methoxy-9-[2-(tetrahydro-2H-pyran-2-yl)ethyl]-9H-Purin-6-amine

HRID 1010984Notes

Reaction equation

FC(F)(F)C(O)=O.[CH2:8]([O: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][CH2:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][O:39]1)(=O)=O>CN(C=O)C>[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:36][CH2:37][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][O:39]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate salt (200 mg) and potassium carbonate (236 mg) in dry DMF (2 mL) were heated at 60° C. with stirring for 1 h. 2-(Tetrahydro-2H-pyran-2-yl)ethyl methanesulfonate (142 mg) was added and the reaction was continued for 16 h at 60° C. The mixture was quenched with water and extracted with EtOAc (×3). The combined organics were washed with water and brine, dried using a hydrophobic frit and evaporated to give crude material (540 mg). The material was purified by normal phase chromatography (ISCO) using 0-20% methanol/EtOAc as eluent to give the title compound as a white solid (88 mg).

Workup

waitthe reaction was continued for 16 h at 60° C
customThe mixture was quenched with water
extractionextracted with EtOAc (×3)
washThe combined organics were washed with water and brine
customdried
customevaporated
customto give crude material (540 mg)
customThe material was purified by normal phase chromatography (ISCO)

Sources & evidence

ORD record: ord-fd93985a397b4e18bcdcf7f23cd3d698
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977344B2

Reaction notes

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