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CAS No. : | 672-41-3 | MDL No. : | MFCD08436657 |
Formula : | C5H4F3N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FIAIKJQZLXLGCR-UHFFFAOYSA-N |
M.W : | 163.10 | Pubchem ID : | 22385756 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 31.44 |
TPSA : | 51.8 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.79 cm/s |
Log Po/w (iLOGP) : | 1.06 |
Log Po/w (XLOGP3) : | 0.71 |
Log Po/w (WLOGP) : | 2.24 |
Log Po/w (MLOGP) : | 0.11 |
Log Po/w (SILICOS-IT) : | 1.25 |
Consensus Log Po/w : | 1.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.64 |
Solubility : | 3.77 mg/ml ; 0.0231 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.38 |
Solubility : | 6.87 mg/ml ; 0.0421 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.17 |
Solubility : | 1.1 mg/ml ; 0.00676 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.63 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
98% | With ammonia In water; acetonitrile at 25℃; for 12 h; | Method 30 4-Amino-6-trifluoromethylpyrimidine A solution of 4-chloro-6-trifluoromethylpyrimidine (1.7 g, 9.9 mmol) in CH3CN (50 ml) was treated with 25percent ammonia(aq) (80 ml). The mixture was stirred at 25° C. for ~12 h. The reaction mixture was quenched with H2O and extracted with EtOAc. The organics were dried with NaCl(sat) and then Na2SO4(s). The organics were removed under reduced pressure to give 1.5 g (98percent) of the title compound as a white solid. NMR: 6.80 (s, 1H); 7.52 (brs, 2H); 8.49 (s, 1H). |
920 mg | With ammonia In methanol at 70℃; for 15 h; Sealed tube | Add 6-(trifluoromethyl)pyrimidin-4-ol (1.5 g, 9.15 mmol) and oxalyl chloride (2.3 mL, 22.9 mmol) to EtOAc (15 mL), then add 5 drops of DMF. Heat the mixture to reflux for 2 hrs. After reaction, partition between EtOAc and brine, separate the organic layer; dry the organic layer over anhydrous Na2SO4. Transfer the organic solution to a sealed tube, add a solution of NH3 in methanol (7M, 10 mL), seal the tube, heat at 70° C. for 15 hrs. Cool to room temperature; concentrate under reduced pressure to get the crude product. Purification by chromatography (silica gel, EtOAc:PE=2:1) affords the target compound (920 mg, 61.3percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | Stage #1: for 7 h; Heating / reflux Stage #2: With ammonia In water at 20℃; |
Preparation of 6-Trifluoromethyl-pyrimidin-4-ylamine; The procedure was derived from methods described in US 5,756,275 and WO 02/38569. In a 250 mL round bottom flask, 6-trifluorornethyl-4-pyrimidinol (10 g, 60.9 mmol) was dissolved in 70 mL phosphorus oxychloride (0.73 mol). The solution was heated at reflux for 7 h. The cooled reaction solution was then added gradually to 200 mL 30percent ammonium hydroxide, and the resulting mixture was stirred overnight at room temperature. The reaction mixture was extracted with ethyl acetate (2 x 100 mL), and the combined extracts were dried (MgSO4) and evaporated in vacuo to give 6-trifluoromethyl-pyrimidin-4-ylamiπe (1.4 g, yield 14percent) as a white solid. 1H NMR (400 MHz, DMSO-dβ) δ 8.50 (s, 1 H), 7.60 (broad s, 2 H), 6.90 (s, 1 H); LC-MS m/z 164.1 [M+Hf. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61.3% | Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In ethyl acetate for 2 h; Reflux Stage #2: at 70℃; for 15 h; Sealed tube |
Add 6-(trifluoromethyl)pyrimidin-4-ol (1.5 g, 9.15 mmol) and oxalyl chloride (2.3 mL, 22.9 mmol) to EtOAc (15 mL), then add 5 drops of DMF. Heat the mixture to reflux for 2 hrs. After reaction, partition between EtOAc and brine, separate the organic layer; dry the organic layer over anhydrous Na2S04. Transfer the organic solution to a sealed tube, add a solution of NH3 in methanol (7M, lOmL), seal the tube, heat at 70°C for 15 hrs. Cool to room temperature; concentrate under reduced pressure to get the crude product. Purification by chromatography (silica gel, EtOAc:PE=2:l) affords the target compound (920 mg, 61.3percent). |
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