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[ CAS No. 100643-27-4 ] {[proInfo.proName]}

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Chemical Structure| 100643-27-4
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Product Details of [ 100643-27-4 ]

CAS No. :100643-27-4 MDL No. :MFCD00006098
Formula : C4H6N4O Boiling Point : -
Linear Structure Formula :- InChI Key :SWELIMKTDYHAOY-UHFFFAOYSA-N
M.W : 126.12 Pubchem ID :135408763
Synonyms :

Calculated chemistry of [ 100643-27-4 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 3.0
Molar Refractivity : 32.86
TPSA : 98.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.62
Log Po/w (XLOGP3) : -0.51
Log Po/w (WLOGP) : -0.64
Log Po/w (MLOGP) : -1.06
Log Po/w (SILICOS-IT) : -0.84
Consensus Log Po/w : -0.48

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.79
Solubility : 20.3 mg/ml ; 0.161 mol/l
Class : Very soluble
Log S (Ali) : -1.08
Solubility : 10.5 mg/ml ; 0.083 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.32
Solubility : 60.6 mg/ml ; 0.481 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.1

Safety of [ 100643-27-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 100643-27-4 ]

* 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 [ 100643-27-4 ]
  • Downstream synthetic route of [ 100643-27-4 ]

[ 100643-27-4 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 100643-27-4 ]
  • [ 156-83-2 ]
Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 1914,1917
  • 2
  • [ 50-01-1 ]
  • [ 105-56-6 ]
  • [ 100643-27-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 1, p. 318 - 324
[2] Australian Journal of Chemistry, 2007, vol. 60, # 2, p. 120 - 123
  • 3
  • [ 55034-35-0 ]
  • [ 100643-27-4 ]
Reference: [1] Chemische Berichte, 1900, vol. 33, p. 1375[2] Chem. Zentralbl., 1900, vol. 71, # II, p. 1168
[3] Chemische Berichte, 1900, vol. 33, p. 1375[4] Chem. Zentralbl., 1900, vol. 71, # II, p. 1168
[5] Chemische Berichte, 1900, vol. 33, p. 1375[6] Chem. Zentralbl., 1900, vol. 71, # II, p. 1168
[7] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1190
[8] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1190
[9] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1190
  • 4
  • [ 18852-51-2 ]
  • [ 113-00-8 ]
  • [ 100643-27-4 ]
Reference: [1] Organic Syntheses, 1952, vol. 32, p. 45
[2] Chemische Berichte, 1913, vol. 46, p. 3844
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1191
  • 5
  • [ 113-00-8 ]
  • [ 105-56-6 ]
  • [ 100643-27-4 ]
  • [ 55034-35-0 ]
Reference: [1] Chemische Berichte, 1900, vol. 33, p. 1375[2] Chem. Zentralbl., 1900, vol. 71, # II, p. 1168
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1190
  • 6
  • [ 100643-27-4 ]
  • [ 6312-72-7 ]
Reference: [1] Journal of Organic Chemistry, 1956, vol. 21, p. 567,571
[2] Biochimica et Biophysica Acta, 1953, vol. 12, p. 462,474
  • 7
  • [ 100643-27-4 ]
  • [ 2032-35-1 ]
  • [ 7355-55-7 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With hydrogenchloride In water at 90℃; for 0.5 h;
Stage #2: With sodium acetate In water at 0 - 80℃; for 3.5 h;
To a suspension of bromoacetaldehyde diethyl acetal (10.4 mL,68.98 mmol) in water (35 mL) was added concentrated hydrochloric acid (1.5 mL). The reaction mixture was stirred at 90 °C. After 30 min,the solution was cooled to room temperature, and sodium acetate(6.8 g, 82.75 mmol) was added. The mixture solution was added to a suspension of 2,6-diamino-4-pyrimidinone (10.0 g, 79.29 mmol) and sodium acetate (3.5 g, 42.82 mmol) in water (75 mL). The reaction mixture was stirred at 80 °C. After 2 h, the mixture was stirred at 0 °Cfor 90 min. The precipitate was filtered off, and washed with a little amount of cold water and acetone to afford the title product (11.9 g,quantitative yield); 1H NMR (300 MHz, DMSO‑d6) δ 10.97 (s, 1H),10.23 (s, 1H), 6.61–6.60 (m, 1H), 6.18–6.17 (m, 1H), 6.05 (s, 2H).
74%
Stage #1: With hydrogenchloride In water at 90℃; for 0.5 h;
Stage #2: With sodium acetate In water at 0 - 80℃; for 3.5 h;
Step one: After adding Sm-1 (27.3 g, 138 mmol) to 70 mL of water, an additional 3.0 mL of concentrated hydrochloric acid was added and stirred at 90 ° C for 0.5 h. After cooling to room temperature, sodium acetate (13.6 g, 165 mmol) (7.0 g, 85.4 mmol) was dissolved in 150 mL of water and stirred for 2 h at 80 ° C. The mixture was stirred at 0 ° C for 1.5 h, filtered, and washed with ice-water (20.0 g, 159 mmol) and sodium acetate And acetone, and dried to give 15.4 g of a yield of 74percent.
74%
Stage #1: With hydrogenchloride In water at 90℃; for 0.5 h;
Stage #2: With sodium acetate In water at 80℃; for 2 h;
After Sm-1 (27.3 g, 138 mmol) was added to 70 mL of water, 3.0 mL of concentrated hydrochloric acid was added and the mixture was stirred at 90 ° C. for 0.5 h.After cooling to room temperature, sodium acetate (13.6 g, 165 mmol) was added and stirred,Sm-2 (20.0 g, 159 mmol) and sodium acetate (7.0 g, 85.4 mmol) were dissolved in 150 mL of water and added to the reaction. After stirring for 2 h at 80 ° C the reaction mixture was shifted to zero degrees Celsius for 1.5 h, filtered, Water and acetone, pumping dry 15.4g, yield 74percent.
42%
Stage #1: With hydrogenchloride In water at 90℃; for 0.5 h;
Stage #2: With sodium acetate In water at 80℃; for 2 h;
Bromoacetaldehyde diethyl acetal (1.1 mL, 0.91 equiv) was suspended in water (4.0 mL) and cone, hydrochloric acid (0.15 mL) was added. The mixture was stirred at 90 °C until a clear solution was formed (approximately 30 min). The solution was cooled to room temperature and sodium acetate (0.71 g) was added. This mixture was added to a suspension of 2,6-diamino- 4-pyrimidinone (1.0 g, 7.93 mmol, 1.00 equiv) and sodium acetate (0.35 g) in water (10 mL). The resulting mixture was stirred at 80 °C for 2 h. During this period the suspension first dissolved partially, before a white solid gradually precipitated. The obtained suspension was stirred at 0 °C for 90 min. The precipitate was collected and washed with a small amount of cold water and acetone. Drying in vacuo yielded 2-amino-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one (0.5 g, 42 percent) as white solid.

Reference: [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 21, p. 5596 - 5611
[2] European Journal of Organic Chemistry, 2010, # 34, p. 6517 - 6519
[3] Patent: CN103601779, 2016, B, . Location in patent: Paragraph 0057; 0058; 0059
[4] Patent: CN104292117, 2016, B, . Location in patent: Paragraph 0476; 0499-0501
[5] Patent: WO2014/11911, 2014, A2, . Location in patent: Paragraph 00252; 00253; 00254
  • 8
  • [ 107-20-0 ]
  • [ 100643-27-4 ]
  • [ 7355-55-7 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: at 20℃; for 0.25 h;
Stage #2: at 20℃; for 46 h;
The mixture Sm-2 (12. 6g, 100mmol) was dissolved in 120mL DMF and 20mL of water, stirred at room temperature after 15min, was added Sm-1 (12. 7mL, 100mmol), stirred for 46h at room temperature the solvent was spin-solid was dissolved in 2. 5mL water was filtered and dried in vacuo to give 12. 9g worm 86percent yield.
74% With sodium acetate In water; N,N-dimethyl-formamide at 20℃; for 48 h; The mixture of 14 2,4-diamino-6-hydroxypyrimidine (1, 5.14g; 0.04mol) and 15 sodium acetate (3.34g; 0.04mol) was dissolved in the mixture of 16 DMF:17 H2O (5:1) at room temperature. Then, 18 chloroacetaldehyde (5.22mL) was added and the mixture was stirred for 48h at room temperature. After completion of the reaction, solvent was evaporated under vacuum and the brown solid was dissolved in 19 water (25mL). The resulting precipitate was filtered. The filtrate was evaporated until one third of the solvent volume was remained and the 20 ethanol was added. The resulting precipitate was collected and washed with little cold water and acetone to afford the 21 compound 3 (5.28g, 74percent) as beige solid [42].
Reference: [1] Patent: CN103819523, 2016, B, . Location in patent: Paragraph 0045; 0046; 0047
[2] Bioorganic Chemistry, 2019, vol. 83, p. 511 - 519
[3] Synlett, 2005, # 5, p. 744 - 750
[4] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2444 - 2454
[5] Patent: CN104672241, 2018, B, . Location in patent: Paragraph 0055-0057
  • 9
  • [ 100643-27-4 ]
  • [ 17157-48-1 ]
  • [ 7355-55-7 ]
YieldReaction ConditionsOperation in experiment
40%
Stage #1: With hydrogenchloride In water at 90℃; for 1 h;
Stage #2: With hydrogenchloride; sodium acetate trihydrate In water at 80℃; Cooling with ice
Add bromoacetaldehyde (9.4 mL, 1.0 eq) to water (40 mL) and add hydrochloric acid (2 mL) while stirring.The reaction was heated to 90° C. for 1 hour. After the reaction was completed, the reaction mixture was cooled with ice water, and sodium acetate trihydrate (12 g, 1.1 eq.) was added thereto to give a reaction solution.Then 2,4-diamino-6-hydroxypyrimidine compound 2302 (10 g, 0.080 mol) was added to water (80 mL) and sodium acetate trihydrate (7.6 g) was added.The aforementioned reaction solution was added, heated to 80C, and reacted overnight. TLC tests showed that the reaction was complete.The reaction solution was stirred under ice for two hours, filtered, and the cake was washed with water. The filter cake was dissolved as much as possible with 95percent ethanol, dissolved three times, the ethanol phases were combined, and the solution was spin-dried to obtain a red-purple solid 2303 (4.7 g, yield: 40percent).
Reference: [1] Patent: CN107722013, 2018, A, . Location in patent: Paragraph 0044; 0045; 0046; 0047; 0048; 0049
  • 10
  • [ 100643-27-4 ]
  • [ 7252-83-7 ]
  • [ 7355-55-7 ]
Reference: [1] Acta Pharmacologica Sinica, 2017, vol. 38, # 7, p. 1059 - 1068
  • 11
  • [ 100643-27-4 ]
  • [ 53106-70-0 ]
  • [ 69205-79-4 ]
YieldReaction ConditionsOperation in experiment
10.11 g With sodium acetate In water at 100℃; Inert atmosphere Methyl formate (18.0 mL, 17.48 g, 291.4 mmol) in toluene (8 mL) was added at 0 °C to a stirred suspension ofNaOMe (14.30 g, 264.9 mmol) in toluene (200 mL). This was followed by dropwise addition of chloroacetonitrile (16.8 mL, 20.00 g, 264.9 mmol) in toluene (60 mL) over 1 h. The reaction mixture was stirred for 3 h followed by addition of H2O (150 mL). The organic layer was separated and the aqueous layer was acidified to pH 5 using 6 M HCl and subsequently extracted with EtOAc (3 × 100 mL). The organic layers were combined and dried over MgSO4 and concentrated in vacuo (40 °C, 70 mbar). The dark residue was suspended in H2O (60 mL) and added to a solution of NaOAc (16.39 g, 199.8 mmol) and 2,6-diaminopyrimidin-4(3H)-one(12.00 g, 95.2 mmol) in H2O (200 mL) (previously stirred at 100 °C until complete dissolution). The reaction was refluxed for 16 h. After cooling to room temperature the suspension was filtered and washed with H2O (2 ×20 mL), acetone (2 × 10 mL) and Et2O (2 × 40 mL) to yield 1 (10.11 g, 60percent) as a light tan solid.
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 28, p. 9015 - 9021
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1993 - 2003
[3] Synthetic Communications, 1996, vol. 26, # 17, p. 3317 - 3322
[4] Journal of Enzyme Inhibition and Medicinal Chemistry, 2013, vol. 28, # 5, p. 1080 - 1087
[5] Archiv der Pharmazie, 2008, vol. 341, # 2, p. 113 - 120
[6] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1333 - 1338
  • 12
  • [ 100643-27-4 ]
  • [ 107-31-3 ]
  • [ 107-14-2 ]
  • [ 69205-79-4 ]
Reference: [1] Helvetica Chimica Acta, 2005, vol. 88, # 10, p. 2610 - 2616
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 16, p. 7043 - 7066
  • 13
  • [ 100643-27-4 ]
  • [ 53106-70-0 ]
  • [ 69205-79-4 ]
Reference: [1] Synthetic Communications, 1996, vol. 26, # 17, p. 3317 - 3322
  • 14
  • [ 100643-27-4 ]
  • [ 2065-75-0 ]
  • [ 120040-42-8 ]
Reference: [1] Patent: US2005/85492, 2005, A1, . Location in patent: Page/Page column 25
  • 15
  • [ 100643-27-4 ]
  • [ 120040-42-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 18, p. 3388 - 3398
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