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CAS No. : | 84955-31-7 | MDL No. : | MFCD07369229 |
Formula : | C6H5ClN4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VIVLSUIQHWGALQ-UHFFFAOYSA-N |
M.W : | 168.58 | Pubchem ID : | 5324413 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 43.3 |
TPSA : | 67.59 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) : | -6.42 cm/s |
Log Po/w (iLOGP) : | 1.21 |
Log Po/w (XLOGP3) : | 1.28 |
Log Po/w (WLOGP) : | 1.2 |
Log Po/w (MLOGP) : | 0.6 |
Log Po/w (SILICOS-IT) : | 1.49 |
Consensus Log Po/w : | 1.16 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.3 |
Solubility : | 0.851 mg/ml ; 0.00505 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.3 |
Solubility : | 0.847 mg/ml ; 0.00503 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.79 |
Solubility : | 0.274 mg/ml ; 0.00163 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.59 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H319 | 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 |
---|---|---|
78% | for 2 h; Reflux | The G005 (10. 0g, 66. 6mmol) was added to lOOmLPOCl3, refluxed for 2h, the solvent spin After cooling to room temperature, the reaction was added to 120mL of ice water, and the solid was filtered, and the filtrate was washed with aqueous ammonia solution to pH = 2, and the ice bath and the precipitate As 2h after filtration, the solid was filtered and washed first with ice water 10mL, 30mL second ice was washed with ether, was drained after 8. 7g, 78percent yield . |
64% | for 1.5 h; Reflux | Phosphorus oxychloride (32 mL) and 7-deazaguanine (0.80 g, 5.33 mmol) were heated under reflux for 1hr 30min. After cooling the mixture was concentrated under high vacuum. Later some ice was cautiously added and then some water. The mixture was then neutralized with sodium hydrogen carbonate salt. The precipitated solid was filtered off and dried to yield (0.57 g, 3.4 mmol, 64percent) of the chlorinated final material. 1H NMR (500 MHz, d-CDCl3) δH (ppm): 8.30 (broad s, 1H, NH-9), 7.00 (s, 1H, H-8), 6.45 (s, 1H, H7), 4.95 (broad s, 2H, NH2-2). 13C NMR (126 MHz, d-CDCl3) δC (ppm): 153.19 (s, C-2), 151.78 (s, C-4), 150.68 (s, C-6), 122.09 (s, C-8), 111.98 (s, C-5), 100.78 (s, C-7). |
53% | at 110℃; for 5 h; | 2-Amino-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one (500 mg, 3.33 mmol, 1.00 equiv) was dissolved in phosphorus oxychloride (3 mL). The resulting solution was stirred for 5 h at 110°C. The reaction was quenched by the addition of 20 mL of water/ice. The resulting solution was extracted with 3x50 mL of dichloromethane and the organic layers were combined and concentrated under vacuum. The residue was purified by silica gel column chromatography with dichloromethane/methanol (1 : 10). This resulted in 0.3 g (53percent) of 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine as a light yellow solid. |
45% | Stage #1: With N-benzyl-N,N,N-triethylammonium chloride; 2,3-Dimethylaniline; trichlorophosphate In acetonitrile at 20 - 85℃; for 3.5 h; Stage #2: With ammonia In water |
Step A2:4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine. To a solution of 2-amino-3,7-dihydro- pyrrolo[2,3-d]pyrimidin-4-one (5.00 g, 33.3 mmol), dimethylaniline (4.22 mL, 41.0 mmol) and benzyltriethylammonium chloride (15.2 g, 66.6 mmol) in acetonitrile (25 mL) at room temperature under argon was added POCl3 (18.6 mL, 200 mmol) dropwise for 30 min. The mixture was refluxed at 850C for 3 h and cooled to room temperature. The reaction was concentrated in vacuo to brown oil and to the oil was added an ice cold H2O (10 mL). The pH of the solution was adjusted to 5 by the addition of an aqueous NH4OH solution. Silica gel chromatography (CH2Cl2:Me0H = 95: 5) yielded 2.53 g (45percent) of 4-chloro-7H- pyrrolo[2,3-d]pyrimidin-2-ylamine as a light yellow solid. The product was then benzylated at N7 using standard techniques. |
23% | With trichlorophosphate In <i>N</i>,<i>N</i>-dimethyl-aniline for 3 h; Reflux | Step 1. Creation of the heterocycle (FIG. 3). To a solution of 2,4-diamino-6-hydroxypyrimidine (1, 25.2 g) in DMF (480 mL) and water (80 mL) was added sodium acetate (27.2 g). The resulting yellow solution was stirred for 1 h. To the solution was added chloroacetaldehyde (50percent solution, 25.4 mL) and the mixture was stirred at rt for 2 days. The volatiles were removed in vacuo and the residue was mixed with methanol (70 mL) and stored at rt overnight. The resulting solid was filtered. The solid was mixed with methanol (150 mL) and heated at 60° C. for 10 min and cooled to rt overnight. The resulting solid was filtered and dried. The yield of 2 was 15 g to 19 g. (0032) A mixture of 7-deazaguanine (14.2 g) and dimethylaniline (6 mL) in POCl3 (200 mL) was refluxed for 3 h (bath temp. 130° C.). After cooling to rt, volatiles were removed by distillation (bath temp 60° C.). The residue was mixed with water (2300 mL) and neutralized with ammonium hydroxide until complete precipitation of solid (pH4). The resulting precipitate was filtered and further purified by column chromatography (silica, MC:MeOH=10:1) to give 3.6 g (21.4 mmol, 23percent) of solid (FIG. 3). |
10% | Stage #1: for 4 h; Reflux Stage #2: With ammonium hydroxide In waterCooling with ice |
To a round-bottomed flask were added 26 (3 g, 19.9 mmol) of and three drops of N,N'-dimethyl aniline. The mixture was suspended on phosphorus oxychloride (250 mL). The reaction was continued at reflux for 4 h. After cooling to room temperature, the solvent was evaporated under reduced pressure and the residue was treated with ice water (20 mL) in an ice bath. The pH of the suspension was adjusted to 7 with concentrated ammonium hydroxide solution. The precipitate was filtered, air-dried and then dissolved in methanol. Silica gel (6 g) was added to the solution which was then evaporated to dryness to form a plug. The silica gel plug obtained was loaded onto a silica gel column and eluted with 2percent methanol in chloroform. Fractions corresponding to the product (TLC) were pooled and evaporated to dryness under reduced pressure to afford 27 (10percent) as a sparkling white solid: mp 215-216 °C; TLC Rf 0.56 (CHCl3/CH3OH, 5:1 with two drops of concentrated NH4OH); 1H NMR (DMSO-d6): δ 6.24 (s, 1H, C5-CH), 6.49 (br s, 2H, NH2, exch), 7.08 (s, 1H, C6-CH), 11.46 (s, 1H, NH, exch). Anal. (C6H5ClN4*0.25H2O) C, H, N, Cl. |
10% | at 110℃; for 2 h; | Compound 21 3 (2.95g; 0.02mol) was suspended in 24 POCl3 (25mL) and the mixture was refluxed for 2h. After cooling to room temperature, excess of POCl3 was evaporated under vacuum and the residue was treated with 25 ice water. The resulting precipitate was filtered off and the pH of the filtrate was adjusted to 7 with aqueous ammonia. Then, the filtrate was extracted with EtOAc (3×50mL). The organic phase was dried over sodium sulfate and evaporated to afford 26 compound 4 (0.33g, 10percent), which was used for the next reaction without further purification [42]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With ammonia In methanol; water for 17 h; | To a suspension of 2-AMINO-4- CHLORO-7H-PYRROLO [2, 3-d] pyrimidine (1) (1.0 g, 6.0 mmol) in MeOH (50 mL) and aqueous ammonium hydroxide (1 mL) was added 10percent Pd-C (500 mg). The reaction mixture was stirred under atmospheric pressure for 17 h and the catalyst was filtered through A pad of Celite. The filtrate was concentrated and chromatographed with silica gel (CH2CL2 : MEOH = 90: 10) to yield 717 mg of the target compound (90percent). H NMR (DMSO-D6) : 8 11.4 (bs, 1H), 8. 50 (s, 1 H), 7.11 (dd, J= 3. 6,0. 6 HZ, 1H), 6.49 (bs, 2H), 6.32 (dd, J= 3. 6,0. 9 HZ, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | Stage #1: With antimony(III) chloride In 1,2-dichloro-ethane at -10℃; for 0.0833333 h; Stage #2: With tert.-butylnitrite In 1,2-dichloro-ethane at -10℃; for 3 h; |
Example 7 EPO <DP n="32"/>2,4-dichIoro-7H-pyrrolo[2,3-d]pyrimidine. To a suspension of 4-chloro-7H-pyrrolo[2,3- d]pyrimidin-2-ylamine (500 mg, 2.97 mmol) in 1,2-dichloroethane (40 niL) at -1O0C under argon was added antimony chloride (750 mg, 3.29 mmol). After stirring for 5 min, tert- butylnitrite (2.50 mL, 20.8 mmol) was added to the solution. The reaction was stirred at -1O0C for 3 h. The reaction was diluted with CHCl3 (100 mL) and poured into ice water (50 mL). The CHCl3 layer was separated, washed with brine (20 mL), dried with Na2SO4, and concentrated to dryness. Silica gel chromatography (Hexanes:EtOAc = 50:50) yielded 239 mg (43percent) of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine as a tan solid. |
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