Structure of 97603-38-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only! Not for Human Use. We Do Not Sell to Patients.
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| CAS No. : | 97603-38-8 |
| Formula : | C9H6ClN3 |
| M.W : | 191.62 |
| SMILES Code : | ClC1=NC(C2=NC=CC=C2)=NC=C1 |
| English Name : | 4-Chloro-2-(pyridin-2-yl)pyrimidine |
| MDL No. : | MFCD11046846 |
| InChI Key : | ARGBHRKAKVWOEC-UHFFFAOYSA-N |
| Pubchem ID : | 13590375 |
| Num. heavy atoms | 13 |
| Num. arom. heavy atoms | 12 |
| Fraction Csp3 | 0.0 |
| Num. rotatable bonds | 1 |
| Num. H-bond acceptors | 3.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 50.27 |
| TPSA ? Topological Polar Surface Area: Calculated from |
38.67 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.92 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.79 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.19 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.97 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.61 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.9 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-2.77 |
| Solubility | 0.323 mg/ml ; 0.00169 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-2.22 |
| Solubility | 1.15 mg/ml ; 0.00602 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.42 |
| Solubility | 0.00735 mg/ml ; 0.0000384 mol/l |
| Class? Solubility class: Log S scale |
Moderately soluble |
| GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
| BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
| P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
| CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
| CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
| CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
| CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
| CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
| Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.2 cm/s |
| Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
| Ghose? Ghose filter: implemented from |
None |
| Veber? Veber (GSK) filter: implemented from |
0.0 |
| Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
| Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
| Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
| PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
| Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
| Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
| Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.88 |
* 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 |
|---|---|---|
| 76% | With hydrazine hydrate In ethanol for 1h; Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 94% | With trichlorophosphate for 3h; Heating; | |
| 93% | With trichlorophosphate In 1,2-dichloro-ethane Heating; | |
| 93% | With trichlorophosphate In dichloromethane at 80℃; for 1h; | 4-Chloro-2-pvridin-2-vl-pyrimidine; 2-Pyridin-2-yl-3H-pyrimidin-4-one, (0.945g, 5.45 mmol) was stirred in dichloromethane (25 mL) and phosphorous oxychloride (10 mL, 107 mmol) at 80°C for 1 h. The phosphorous oxychloride and dichloromethane was removed by vacuo. Crushed ice (50 mL) was added to the reaction mixture followed by K2CO3 (1 M, aq. ) until pH reached 7. The resulting mixture was extracted with ethyl acetate (3x50 mL). The combined organic layers were extracted with brine (1x30 mL) and dried (MgS04). The solvent was evaporated to give the title compound (0.975 g, 93%). 'H NMR (400 MHz, dmso-d6) 8 7.6 (t, J=5. 5 Hz, 1 H) 7.8 (d, J=5. 1 Hz, 1 H) 8.0 (td, J=7. 8,1. 2 Hz, 1 H) 8.4 (d,. J=7. 7 Hz, 1 H) 8.8 (m, 1 H) 8.9 (d, J=5. 0 Hz, 1 H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In N,N-dimethyl-formamide at 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 58% | In N,N-dimethyl-formamide at 20℃; | A 4 .-2-peridin-2-vI-pyrimidine; 4-Chloro-2-pyridin-2-yl-pyrimidine (0. 04g, 0. 24mmol) and 3-chloro-benzenethiol (0.07g, 0. 47mmol) were stirred in dimethylformamide (0.5 ml) at room temperature over night. The solvent was evaporated and the reaction mixture was purified by HPLC : Waters Fraction- Lynxsystem with UV, ELSD and MS ; Column: Ace C8 5µ 100 mm x 21,2 mm id, to give the title compound (0.042g, yield 58%). IH NMR (400 MHz, dmso-d6) 8 7.0 (d, J=5. 2 Hz, 1 H) 7.5-7. 6 (m, 2 H) 7.7 (t, J=7. 5 Hz, 2 H) 7.9 (t, J=2. 0 Hz, 1 H) 8.0 (m, 1 H) 8.7 (d, J=4. 0 Hz, 1 H) 8.7 (m, 2 H). |
| In N,N-dimethyl-formamide at 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In N,N-dimethyl-formamide at 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In N,N-dimethyl-formamide at 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In N,N-dimethyl-formamide at 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In N,N-dimethyl-formamide at 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 53% | With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 1.25h; | B Method B; 4- (3, 4-Difluorophenylthio]-2-pyridin-2-ylpyrimidine; To a solution of 4-chloro-2-pyridin-2-yl-pyrimidine (0.054 g, 0.28 mmol) and 3,4- difluorothiophenol (32 mL, 0.28 mmol) in dry DMF was added at 0 °C NaH (95 %, 0.009 g, 0.28 mmol) and the reaction was stirred at 0 °C under a nitrogen atmosphere for 1 h 15 min. NaOH (1M) and EtOAc were added and the layers separated. The aqueous phase was extracted with EtOAc (3x). Combined organic phases were washed (water and brine), dried (MgSO4), filtered and evaporated under reduced pressure, followed by preparative HPLC purification to give 0.045 g (53 %) of the title compound. 'H NMR (400 MHz, DMSO-d6) 8 7.06 (d, 1H), 7.53 (m, 1H), 7.64 (m, 2H), 7.95 (m, 2H), 8.21 (d, 1H), 8.66 (d, 1H), 8.73 (m, 1H) ; LC-MS (API-ES) m/z 302 (M++1). |
| In N,N-dimethyl-formamide at 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With triethylamine In tetrahydrofuran Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With potassium <i>tert</i>-butylate In 1,2-dimethoxyethane |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With triethylamine In tetrahydrofuran Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In N,N-dimethyl-formamide at 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: 54 percent / NaOEt / ethanol / 18 h / Heating 2: 93 percent / POCl3 / 1,2-dichloro-ethane / Heating |