Identification | Back Directory | [Name]
2,4-DICHLORO-5,7-DIHYDROFURO[3,4-D]PYRIMIDINE | [CAS]
848398-41-4 | [Synonyms]
2,4-dichloro-5H,7H-furo[3,4-d]pyrimidine 2,4-DICHLORO-5,7-DIHYDROFURO[3,4-D]PYRIMIDINE Furo[3,4-d]pyrimidine, 2,4-dichloro-5,7-dihydro- 2,4-dichloro-5,7-dihydrofurano [3,4-d] pyrimidine | [Molecular Formula]
C6H4Cl2N2O | [MDL Number]
MFCD13250060 | [MOL File]
848398-41-4.mol | [Molecular Weight]
191.01 |
Chemical Properties | Back Directory | [Boiling point ]
337.8±42.0 °C(Predicted) | [density ]
1.592±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [pka]
-3.43±0.20(Predicted) | [Appearance]
Light yellow to brown Solid |
Hazard Information | Back Directory | [Uses]
2,4-Dichloro-5,7-dihydrofuro[3,4-d]pyrimidine is used as a reagent in the synthesis of substituted pyrimidinediamines as potent dual BRD4-kinase inhibitors for treating cancer. | [Synthesis]
The general procedure for the synthesis of 2,4-dichloro-5,7-dihydrofuro[3,4-D]pyrimidine-2,4-diol from 5,7-dihydrofuro[3,4-D]pyrimidine-2,4-diol is as follows: to a solution of trichlorophosphine oxide (30 mL) of 5,7-dihydrofuro[3,4-D]pyrimidine-2,4-diol (500 mg, 3.25 mmol) was added, at 0 °C, a solution of dimethylaniline (500 mg, 4.13 mmol). The reaction mixture was heated to reflux for 12 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was carefully poured into ice (100 g) and extracted with dichloromethane (50 mL x 3). The organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. After filtration to remove the desiccant sodium sulfate, the organic solvent was removed by concentration under reduced pressure. Finally, the crude product was purified by fast column chromatography using a mixed solvent system of hexane and ethyl acetate to afford the target compound 2,4-dichloro-5,7-dihydrofuro[3,4-d]pyrimidine (300 mg, 49% yield). Mass spectrometry (LRMS) analysis showed the m/z value of (M + H+) to be: calculated value 192.01; measured value 192.10. | [References]
[1] Patent: WO2014/15291, 2014, A1. Location in patent: Page/Page column 181; 182 [2] Patent: EP1666468, 2006, A1. Location in patent: Page/Page column 32-33 |
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Shangchem Co., Ltd.
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