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CAS No. : | 186454-70-6 | MDL No. : | MFCD09834959 |
Formula : | C6H5N3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JPIPZNJBXFDXHH-UHFFFAOYSA-N |
M.W : | 135.12 | Pubchem ID : | 9898839 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 36.21 |
TPSA : | 64.94 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.71 cm/s |
Log Po/w (iLOGP) : | 1.09 |
Log Po/w (XLOGP3) : | 0.59 |
Log Po/w (WLOGP) : | 0.81 |
Log Po/w (MLOGP) : | -0.02 |
Log Po/w (SILICOS-IT) : | 0.75 |
Consensus Log Po/w : | 0.65 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.72 |
Solubility : | 2.6 mg/ml ; 0.0193 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.53 |
Solubility : | 4.01 mg/ml ; 0.0297 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.15 |
Solubility : | 0.954 mg/ml ; 0.00706 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.45 |
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 |
---|---|---|
40% | Stage #1: With chloro-trimethyl-silane; tert.-butylnitrite In acetonitrile at 50℃; for 1.5 h; Stage #2: With sodium hydroxide In water; acetonitrile |
4-Chlorofuro[2,3,cflpyrimidine was obtained via modified Sandmeyer reaction25 with 4-amino-furopyrimidine 25.26(25) (a) For the modified Sandmeyer reaction, see: (a) Bracher, F.; Daab, J. Eur. J. Org. Chem. 2002, 2288. (b)Doyle, M. P.; Siegfiied, B.; Dellaria, J. F. J. Org. Chem. 1977, 42, 2426.(26) Nakano, M.; Maeda, Y. WO 2005061516 Al 20050707 CAN 143:115566. EPO <DP n="82"/>The mixture of 4-amino-furopyrimidme 25 (303 mg, 2.24 mmol), tert-butyl nitrite (5.3 niL, 44.6 mmol), TMSCl (1.4 mL, 11.07 mmol) in acetonitrile (5.0 mL) was stirred at 50 0C for 1.5 h. After this period, the mixture was quenched with IN NaOH and the aqueous phase was thoroughly extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography with 10percent EtOAc/hexanes to give 26 (139 mg, 40percent).1H NMR (500 MHz, CDCl3, δ): 8.68 (s, IH), 7.72 (d, J= 2.5 Hz5 IH), 6.84 (d, J = 2.5 Hz5 IH). 13C NMR (125 MHz5 CDCl3, δ): 167.1, 154.0, 153.5, 146.0, 177.9, 104.7. MS m/z (relative intensity) 154 (M+, 100), 119 (37), 98 (21). |
22% | With chloro-trimethyl-silane; tert.-butylnitrite In acetonitrile at 50℃; for 1 h; | Step 3. Synthesis of 4-chlorofuro[2,3-d]pyrimidine (C3). A mixture of C2 (660 mg, 4.88 mmol), terf-butyl nitrite (12.1 mL, 97.7 mmol), and trimethylsilyl chloride (3.12 mL, 24.4 mmol) in acetonitrile (20 mL) was stirred at 50 °C for 1 hour. The reaction was cooled to room temperature and quenched with aqueous sodium hydroxide solution (2 M, 30 mL). The aqueous layer was extracted with ethyl acetate (3 x 50 mL), and the combined organic layers were dried over sodium sulfate. The solvent was removed in vacuo and the residue was purified via chromatography on silica gel (Gradient: 0percent to 30percent ethyl acetate in heptane) to provide the product as a volatile white solid. Yield: 168 mg, 1.09 mmol, 22percent. LCMS m/z 154.8 [M+H]+. 1 H NMR (400 MHz, CDCI3) δ 8.77 (s, 1 H), 7.76 (d, J=0.8 Hz, 1 H), 7.25 (d, J=0.8 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | at 120℃; | Step 2. Synthesis of furo[2,3-d]pyrimidin-4-amine (C2). Compound C1 (100 mg, 0.925 mmol) was dissolved in formamide (2 mL) and the reaction mixture was heated at 120 °C overnight. The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the product as a yellow solid. Yield: 21 mg, 0.16 mmol, 17percent. LCMS m/z 135.9 [M+H]+. 1 H NMR (400 MHz, CD3OD) δ 8.13 (s, 1 H), 7.61 (d, J=2.5 Hz, 1 H), 6.89 (d, J=2.5 Hz, 1 H). |
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