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[ CAS No. 84955-31-7 ] {[proInfo.proName]}

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Chemical Structure| 84955-31-7
Chemical Structure| 84955-31-7
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Product Details of [ 84955-31-7 ]

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 :

Calculated chemistry of [ 84955-31-7 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.59

Safety of [ 84955-31-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 84955-31-7 ]

* 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.

  • Upstream synthesis route of [ 84955-31-7 ]
  • Downstream synthetic route of [ 84955-31-7 ]

[ 84955-31-7 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 7355-55-7 ]
  • [ 84955-31-7 ]
YieldReaction ConditionsOperation 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].

Reference: [1] Liebigs Annalen der Chemie, 1987, p. 15 - 19
[2] Angewandte Chemie - International Edition, 2007, vol. 46, # 13, p. 2325 - 2327
[3] Patent: CN103819523, 2016, B, . Location in patent: Paragraph 0048; 0049; 0050
[4] Liebigs Annalen der Chemie, 1983, # 1, p. 137 - 146
[5] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 7, p. 2260 - 2264
[6] Patent: WO2014/11911, 2014, A2, . Location in patent: Paragraph 00252; 00255; 00256
[7] Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 11, p. 756 - 761[8] Bioorganicheskaya Khimiya, 1995, vol. 21, # 11, p. 874 - 880
[9] Heterocycles, 1993, vol. 35, # 2, p. 825 - 841
[10] Arkivoc, 2016, vol. 2016, # 6, p. 45 - 51
[11] Patent: WO2006/122003, 2006, A2, . Location in patent: Page/Page column 12; 13; 14
[12] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1124 - 1129
[13] Patent: US10059735, 2018, B1, . Location in patent: Page/Page column 4; 5
[14] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2444 - 2454
[15] Bioorganic Chemistry, 2019, vol. 83, p. 511 - 519
[16] Journal of Medicinal Chemistry, 1986, vol. 29, p. 1749 - 1753
[17] Patent: WO2012/45195, 2012, A1, . Location in patent: Page/Page column 60
[18] Patent: WO2012/74999, 2012, A1, . Location in patent: Page/Page column 126; 127
  • 2
  • [ 7355-55-7 ]
  • [ 84955-31-7 ]
Reference: [1] Patent: WO2010/14930, 2010, A2, . Location in patent: Page/Page column 55-56
  • 3
  • [ 52133-67-2 ]
  • [ 84955-31-7 ]
Reference: [1] Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 11, p. 756 - 761[2] Bioorganicheskaya Khimiya, 1995, vol. 21, # 11, p. 874 - 880
  • 4
  • [ 84981-48-6 ]
  • [ 84955-31-7 ]
Reference: [1] Liebigs Annalen der Chemie, 1983, # 1, p. 137 - 146
  • 5
  • [ 63026-85-7 ]
  • [ 84955-31-7 ]
Reference: [1] Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 11, p. 756 - 761[2] Bioorganicheskaya Khimiya, 1995, vol. 21, # 11, p. 874 - 880
  • 6
  • [ 84955-31-7 ]
  • [ 86392-75-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1988, vol. 25, # 6, p. 1893 - 1898
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 697 - 702
[3] Tetrahedron Letters, 1987, vol. 28, # 43, p. 5107 - 5110
[4] Tetrahedron Letters, 1987, vol. 28, # 43, p. 5107 - 5110
  • 7
  • [ 84955-31-7 ]
  • [ 93366-88-2 ]
YieldReaction ConditionsOperation 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).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 18, p. 5261 - 5264
[2] Patent: WO2004/80466, 2004, A1, . Location in patent: Page/Page column 32
[3] Liebigs Annalen der Chemie, 1984, # 10, p. 1719 - 1730
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 1, p. 334 - 337
  • 8
  • [ 84955-31-7 ]
  • [ 90213-67-5 ]
Reference: [1] Liebigs Annalen der Chemie, 1984, # 4, p. 722 - 733
  • 9
  • [ 84955-31-7 ]
  • [ 90213-66-4 ]
YieldReaction ConditionsOperation 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.
Reference: [1] Patent: WO2006/122003, 2006, A2, . Location in patent: Page/Page column 30-31
[2] Liebigs Annalen der Chemie, 1984, # 4, p. 722 - 733
[3] Liebigs Annalen der Chemie, 1985, p. 312 - 320
[4] Patent: WO2012/45195, 2012, A1, . Location in patent: Page/Page column 60
  • 10
  • [ 3282-30-2 ]
  • [ 84955-31-7 ]
  • [ 149765-15-1 ]
Reference: [1] Synthesis, 2004, # 8, p. 1203 - 1210
[2] Heterocycles, 1993, vol. 35, # 2, p. 825 - 841
[3] Angewandte Chemie - International Edition, 2007, vol. 46, # 13, p. 2325 - 2327
[4] Nucleosides and Nucleotides, 1997, vol. 16, # 7-9, p. 941 - 944
[5] Patent: US6093807, 2000, A,
[6] Patent: WO2010/110775, 2010, A1, . Location in patent: Page/Page column 33
  • 11
  • [ 84955-31-7 ]
  • [ 149765-16-2 ]
Reference: [1] Synthesis, 2004, # 8, p. 1203 - 1210
[2] Nucleosides and Nucleotides, 1997, vol. 16, # 7-9, p. 941 - 944
[3] Heterocycles, 1993, vol. 35, # 2, p. 825 - 841
  • 12
  • [ 84955-31-7 ]
  • [ 911397-54-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7786 - 7795
  • 13
  • [ 84955-31-7 ]
  • [ 934524-10-4 ]
Reference: [1] Patent: WO2012/45195, 2012, A1,
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