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CAS No. : | 7781-10-4 | MDL No. : | MFCD00619245 |
Formula : | C7H6ClN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BJGDLOLPALCTJQ-UHFFFAOYSA-N |
M.W : | 167.60 | Pubchem ID : | 265829 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 43.8 |
TPSA : | 30.71 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.2 cm/s |
Log Po/w (iLOGP) : | 2.01 |
Log Po/w (XLOGP3) : | 1.58 |
Log Po/w (WLOGP) : | 1.62 |
Log Po/w (MLOGP) : | 1.11 |
Log Po/w (SILICOS-IT) : | 1.58 |
Consensus Log Po/w : | 1.58 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.48 |
Solubility : | 0.555 mg/ml ; 0.00331 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.84 |
Solubility : | 2.45 mg/ml ; 0.0146 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.71 |
Solubility : | 0.328 mg/ml ; 0.00195 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.38 |
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 |
---|---|---|
94% | With caesium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 1 h; | lodomethane (12.2 mL, 195 MMOL) was added to a solution of 4-Chloro-7H- pyrrolo [2,3-d] pyrimidine (15.0 g, 97.7 MMOL) and cesium carbonate (47.7 g, 146.5 MMOL) IN DMF (200 mL). The reaction mixture was stirred at room temperature 1 h, quenched with H20 (500 mL), and extracted with EtOAc (3X200ML). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash column chromatography (silica, 2: 8X3 : 7 EtOAc: hexanes) provided the title compound as an off-white solid (15.4 g, 94percent). MS: 168.5 (MH+) ; HPLC Rf : 3.45 min. (HPLC method 4); HPLC purity: 96percent. |
83% | Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 0.333333 h; Stage #2: at 0 - 20℃; for 4 h; |
Step 1 : To a stirred solution of 4-chloro-7/-/-pyrrolo[2,3-d]pyrimidine (4 g, 26.143 mmol) in THF (40 mL) was added potassium tertiary butoxide (3.8 g, 33.986 mmol, 1.3 equiv) at 0°C. The reaction mixture was allowed to stir at room temperature for 20 min. Methyl iodide (2.4 mL, 39.215 mol, 1.5 equiv) was added at 0°C to the reaction mixture and stirred for 4h at room temperature. The solvent was evaporated, diluted with ice water (50 mL) and the precipitated solid was filtered & dried in vacuo to give 4-chloro-7-methyl- 7H-pyrrolo[2,3-d]pyrimidine as off white solid (3.6 g, 83 percent). LCMS (ES) m/z = 168.1 [M+H]+. H NMR (400 MHz, DMSO-d6) δ ppm 3.84 (s, 3H), 6.62 (d, J = 3.2 Hz, 1 H), 7.72 (d, J = 3.2 Hz, 1 H), 8.62 (s, 1 H). |
81% | With caesium carbonate In 1-methyl-pyrrolidin-2-one at 15 - 23℃; for 4.5 h; | Add Cs2CO3(845 g, 2.60 mol) at 15 °C to a solution of 4-chloro-7H-pyrrolo[2,3- d]pyrimidine (200 g, 1.29 mol) in N-methyl-2-pyrrolidone (1.20 L). Warm to 23 °C, add Mel (202 g, 1.43 mol) dropwise over 30 min, and stir for 4 h. After this time, pour onto ice-water (2.00 L) and stir for 30 min. Filter, then slurry material in H20 (1.00 L). Filter and dry to give the title compound (180 g, 81percent). ES/MS m/z (35C1) 168.0 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With N-Bromosuccinimide In dichloromethane at 0 - 25℃; for 2 h; | Example 1 5-(1H-1,3-Benzodiazol-2-yl)-7-methyl-N-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine[0122]STEP 1: 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine [Chem. 3]To a stirred solution of 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (WO2005/095357, 6.02 g, 35.9 mmol) in dichloromethane (120 mL) was added N-bromosuccinimide (7.67 g, 43.1 mmol) at 0 oC. The resulting mixture was stirred at room temperature for 2 hrs. The reaction mixture was quenched with saturated sodium bicarbonate aqueous solution (200 mL), and extracted with dichloromethane (200 mL). The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (dichloromethane/ethyl acetate=10/1) to give the title compound (8.27 g, 93percent) as a white solid.;LCMS (Method A) m/z: M+1 247.9; tR = 2.70 min. |
86% | With N-Bromosuccinimide In dichloromethane at 15 - 23℃; for 3 h; | Add N-bromosuccinimide (418 g, 2.35 mol) portionwise over 20 min at 15 °C to a solution of 4-chloro-7-methyl-pyrrolo[2,3-d]pyrimidine (355 g, 2.12 mol) indichloromethane (3.19 L), and stir at 23 °C for 3 h. After this time, filter, wash with H20 (5.32 L), and dry to give the title compound (448 g, 86percent) as a white solid. ES/MS m/z (35C1,79Br) 245.9 (M+H). |
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