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CAS No. : | 29274-23-5 | MDL No. : | MFCD09746272 |
Formula : | C6H5N3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BUEFDJQUUGMUJO-UHFFFAOYSA-N |
M.W : | 135.12 | Pubchem ID : | 335418 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 35.81 |
TPSA : | 50.16 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.9 cm/s |
Log Po/w (iLOGP) : | 0.77 |
Log Po/w (XLOGP3) : | 0.31 |
Log Po/w (WLOGP) : | 0.02 |
Log Po/w (MLOGP) : | 0.44 |
Log Po/w (SILICOS-IT) : | 0.66 |
Consensus Log Po/w : | 0.44 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.54 |
Solubility : | 3.91 mg/ml ; 0.0289 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.93 |
Solubility : | 16.0 mg/ml ; 0.119 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.59 |
Solubility : | 3.49 mg/ml ; 0.0258 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.73 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | at 90℃; | PREPARATION 32 7-Chloropyrazolo[1,5-a]pyrimidine Pyrazolo[1,5-a]pyrimidin-7(4H)-one (0.50g, 3.70 mmols), phosphorus oxychloride (0.88 mL, 9.62 mmols) and diisopropylethylamine (DIEA, 0.13 mL, 0.74 mmols) were mixed and stirred at 90ºC overnight. It was poured onto water/ice, extracted with dichloromethane and washed with brine. It was dried, filtered and concentrated in vacuo. It was purified by chromatography (Silica gel, Hexane/Ethyl acetate 9:1) to afford the expected compound (83 mg, 71percent). LRMS (m/z): 154 (M+1)+ 1H NMR (400 MHz, DMSO-d6) d ppm 6.93 (d, 1 H) 7.43 (d, 1 H) 8.37 (d, 1 H) 8.52 (d, 1 H) |
71% | at 90℃; | Pyrazolo[1 ,5-a]pyrimidin-7(4/-/)-one (0.50g, 3.70 mmols), phosphorus oxychloride (0.88 mL, 9.62 mmols) and diisopropylethylamine (DIEA, 0.13 mL, 0.74 mmols) were mixed and stirred at 90°C overnight. It was poured onto water/ice, extracted with dichloromethane and washed with brine. It was dried, filtered and concentrated in vacuum. It was purified by chromatography (Silica gel, Hexane/Ethyl acetate 9:1 ) to afford the expected compound (83 mg, 71 percent).LRMS (m/z): 154 (M+1 )+ 1H NMR (400 MHz, DMSO-d6) δ ppm 6.93 (d, 1 H) 7.43 (d, 1 H) 8.37 (d, 1 H) 8.52 (d, 1 H) |
71% | at 90℃; | PREPARATION 897-Chloropyrazolo[1 ,5-a]pyrimidinePyrazolo[1 ,5-a]pyrimidin-7(4H)-one (0.50g, 3.70 mmols), phosphorus oxychloride (0.88ml, 9.62 mmols) and diisopropylethylamine (DIEA, 0.13ml, 0.74 mmols) were mixed and stirred at 90°C overnight. It was poured onto water/ice, extracted with dichloromethane and washed with brine. It was dried, filtered and concentrated in vacuum. It was purified by chromatography (Silica gel, Hexane/Ethyl acetate 9:1 ) to afford the expected compound (83mg, 71 percent).LRMS (m/z): 154 (M+1 )+ 1 H N MR (400 MHz, DMSO-d6) d ppm 6.93 (d, 1 H) 7.43 (d, 1 H) 8.37 (d , 1 H) 8.52 (d, 1 H) |
65% | at 90℃; for 2.5 h; | 7-Hydroxypyrazolo[1 ,5-a]pyrimidine (60 g, 444 mmol), phosphorus oxychloride (108 mL, 1.15 mol) and dimethylaniline (10.8 mL, 89 mmol) were added to a 250 mL round- bottomed flask and the contents heated to 90 0C. After 2.5 h, the reaction mixture was allowed to cool and was concentrated. The black residue was poured into a beaker containing crushed ice (600 mL) and the resulting solution kept cold using an ice bath. The aqueous solution was extracted with CH2CI2 (3 χ 150 mL) and the combined organic phase was washed with brine (100 mL). The organic phase was dried and concentrated to yield the desired crude product, 7-chloropyrazolo[1 ,5-a]pyrimidine, (44.2 g, 65percent) as a red solid. As the crude product was sufficiently pure to use in the subsequent step, a small sample was purified by column chromatography (33-66percent EtOAc/hexane) to yield an analytical sample as a white solid. HPLC 95percent; 1H NMR (250 MHz, CDCI3) δ 8.41 (d, J = 4.5 Hz, 1 H), 8.25 (d, J = 2.3 Hz, 1 H)1 6.99 (d, J ~ 4.5 Hz, 1 H), 6.84 (d, J = 2.3 Hz, 1 H); 13C NMR (62.9 MHz, CDCI3) δ 150.0, 148.2, 145.4, 139.0, 108.0, 98.7; MS (APCI) 154 [M+Hf. |
47% | for 72 h; | The compound prepared in preparative example 1 (2.4 g, 17.4 mmol) was stirred in POCl3 (54 mL) and N,N-dimethylaniline (6.7 mL) 3 days. The reaction mixture was concentrated, dissolved in saturated NaHCO3 (2000 mL) and extracted with CH2Cl2, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography using a 2.5percent MeOH in CH2Cl2 solution as eluent (1.3 g, 47percent yield): M+H=154. |
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