Structure of 54568-12-6
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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.
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CAS No. : | 54568-12-6 |
Formula : | C6H9N3 |
M.W : | 123.16 |
SMILES Code : | NC1=NC=NC(C)=C1C |
MDL No. : | MFCD09909808 |
InChI Key : | SMPCNKPYFMZJMO-UHFFFAOYSA-N |
Pubchem ID : | 643252 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 36.37 |
TPSA ? Topological Polar Surface Area: Calculated from |
51.8 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.36 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.62 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.68 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.06 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.06 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.76 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.49 |
Solubility | 4.01 mg/ml ; 0.0325 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.28 |
Solubility | 6.43 mg/ml ; 0.0522 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.02 |
Solubility | 1.17 mg/ml ; 0.00951 mol/l |
Class? Solubility class: Log S scale |
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) |
No |
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 |
-6.61 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) |
1.49 |
* 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 |
---|---|---|
42% | To a solution of 4-chloro-5,6-dimethylpyrimidine D8 (0.18 g, 1.26 mmol) in dry toluene (4 ml) were added sodium t-butoxyde (0.17 g, 1.77 mmol), Pd2(dba)3 (0.12 g, 0.13 mmol), BINAP (0.24 g, 0.38 mmol) and benzophenone imine (0.25 ml, 1.51 mmol). The resulting mixture was degassed (3 x pump/N2) and then heated to 80 0C. After 1 h stirring, the mixture was cooled down to room temperature, diluted with Et2O (100 ml) and filtered through a celite pad. Volatiles were evaporated, the resulting oil was dissolved in THF (20 ml) and HCl (3 M aqueous solution, 0.63 ml, 1.89 mmol) was added. The mixture was stirred at room temperature for 3 h, concentrated under reduced pressure, neutralized with a saturated NaHCO3 aqueous solution and diluted with DCM (50 ml). The inorganic layer was back-extracted with DCM (2 x 50 ml). The collected organic layers were passed through a phase separator tube and evaporated. The orange solid residue was triturated several times with Et2O and dried to afford the title compound D9 (0.067 g, 0.54 mmol, 42% yield). 1H NMR (400 MHz, CDCl3) δ(ppm): 8.38 (s, 1 H), 4.78 (bs, 1 H), 2.43 (s, 3 H), 2.08 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; at 80℃; for 4h; | A solution of 1,1-dimethylethyl (25)-2-(3-bromo-2-oxopropyl)-l-piperidinecarboxylate D2 (0.10 g, 0.31 mmol) and 5,6-dimethyl-4-pyrimidinamine D9 (0.042 g, 0.34 mmol) in DMF (1 ml) was stirred at 80 0C for 4 h. The solvent was evaporated under reduced pressure and the residue purified by flash chromatography on silica gel (from DCM 100 to DCM /MeOH 98/2) and then eluted through a SCX column to afford a crude material (0.018 g) containing the title compound DlO, the corresponding N-Boc protected derivative and some residual 5,6-dimethyl-4-pyrimidinamine. [N-Boc derivative data. UPLC: rt = 0.58 min, peak observed: 345 (M+l). C1QH2SN4O2 requires 344]. The crude was dissolved in DCM (2 ml), TFA (0.50 ml) was added drop wise and the reaction left under stirring for 1 h at room temperature. Volatiles were removed under reduced pressure and the residue eluted through a SCX cartridge to afford a crude material containing the title compound DlO (0.012 g) contaminated with some residual 5,6-dimethyl-4-pyrimidinamine. UPLC: rt = 0.36 min, peak observed: 245 (M+l). C14H20N4 requires 244. |
A137448 [76574-44-2]
4-Amino-6-methylpyrimidine-5-carbonitrile
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A137448 [76574-44-2]
4-Amino-6-methylpyrimidine-5-carbonitrile
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