Potassium Carbonate → HCID 57699602, compound

HRID 1011087Notes

Reaction equation

FC(F)(F)C(O)=O.[CH2:8]([NH:12][C:13]1[NH:21][C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N: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][CH:35]1[CH2:40][CH2:39][O:38][C:37]([CH3:42])([CH3:41])[CH2:36]1>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][CH:35]2[CH2:40][CH2:39][O:38][C:37]([CH3:41])([CH3:42])[CH2:36]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of N2-butyl-8-(methyloxy)-3H-purine-2,6-diamine trifluoroacetate (149 mg, 0.425 mmol) and potassium carbonate (294 mg, 2.126 mmol) in DMF (2 ml) was stirred and heated at 60° C. under nitrogen for one hour. 4-(3-Bromopropyl)-2,2-dimethyltetrahydro-2H-pyran (125 mg, 0.532 mmol) in dry DMF (1 ml) was added and the mixture heated at 60° C. under nitrogen for a further 2.5 hours. The reaction mixture was cooled to room temperature, quenched into water (10 ml) and extracted with DCM:EtOAc (1:1, 2×20 ml). The organic extracts were combined, dried by passage through a hydrophobic frit and concentrated under vacuum. The residue was purified by mass directed autopreparation. Product containing fractions were combined and evaporated to give the title compound (40 mg).

Workup

temperaturethe mixture heated at 60° C. under nitrogen for a further 2.5 hours
temperatureThe reaction mixture was cooled to room temperature
customquenched into water (10 ml)
extractionextracted with DCM:EtOAc (1:1, 2×20 ml)
customdried by passage through a hydrophobic frit
concentrationconcentrated under vacuum
customThe residue was purified by mass
additionProduct containing fractions
customevaporated

Sources & evidence

ORD record: ord-c4d5bfef00824ca8b92a7f49b88ddf93
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977344B2

Reaction notes

Loading…