[ CAS No. 320-67-2 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 320-67-2
Chemical Structure| 320-67-2
Structure of 320-67-2

Quality Control of [ 320-67-2 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 320-67-2 ]

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Product Details of [ 320-67-2 ]

CAS No. :320-67-2MDL No. :MFCD00006539
Formula :C8H12N4O5Boiling Point :534.5°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :244.20Pubchem ID :9444
Synonyms :

Computed Properties of [ 320-67-2 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 320-67-2 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335-H350-H360Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 320-67-2 ]

  • Upstream synthesis route of [ 320-67-2 ]

[ 320-67-2 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 6974-32-9 ]
  • [ 52523-35-0 ]
  • [ 320-67-2 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: at 55℃; for 12.50 h; Industry scale
Stage #2: With methanol; sodium methylate In dimethyl sulfoxide; acetonitrile at 22 - 23℃; for 3.75 h;
Example 2
Coupling of Silyl 5-Azacytosine to Sugar and Deprotection
A mixture of 2-[(trimethylsilyl)amino]-4-[(trimethylsilyl)oxy]-s-triazine (4.5 Kg), 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (8.8 Kg), anhydrous MeCN (34.6 Kg) and TfOH (600 g) were heated at 55° C. for 12.5 hours.
The reaction mixture was cooled to 45° C., DMSO (29 Kg) was added, and the MeCN was evaporated at an internal temperature of <50° C. under vacuum until about 54 L of the solution.
The solution was cooled to 23° C.
MeOH (13.9 Kg) was added followed by a solution of 30percent NaOMe in MeOH solution (2.5 Kg) that was pre-diluted with MeOH (7.0 Kg).
The solution was stirred at 23° C. for 35 minutes.
When the reaction was complete MeOH (90.4 Kg) was added and the resulting slurry was stirred at 22° C. for 3 hours and 10 minutes and was then filtered and washed three times with MeOH (7.0 Kg each).
The cake was dried under vacuum at below 70° C. for 9 hours and 20 minutes to give 3.2 Kg of 98.89percent purity crude azacitidine (71percent yield based on 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose).
Reference: [1] Patent: US2010/36112, 2010, A1. Location in patent: Page/Page column 7
  • 2
  • [ 13035-61-5 ]
  • [ 320-67-2 ]
YieldReaction ConditionsOperation in experiment
41.3%
Stage #1: With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 20.00 h; Heating / reflux
Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 20.00 h;
A mixture of 5-azacytosine (5.0 g, 44.6 mol), HMDS (6.3 mL, 29.8 mol), and TMSCl (6 mL, 47.3 mmol) in acetonitrile (78 mL) was heated to reflux for 20 hours under an inert atmosphere. TMS-triflate (9 mL, 50 mmol) and 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (14.2 g, 44.6 mmol were added directly to the silylated 5-azacytosine in acetonitrile. The addition was performed at ambient temperature and under an inert atmosphere. The reaction mixture was maintained under stirring for 20 hours, then poured over a pre-cooled (0-5° C.) sodium bicarbonate solution (10percent, 500 mL). The resulting mixture was extracted with dichloromethane (3.x.75 mL). The combined organic extract was washed with cooled (0-5° C.) 10percent sodium bicarbonate (2.x.25 mL) and brine (2.x.25 mL), then dried over magnesium sulfate (10.0 g), filtered, and the filtrate concentrated in vacuum to dryness. The off-white foam dissolved in methanol (120 mL) was treated with a solution of 25percent sodium methoxide in methanol (1.0 g, 4.62 mmol). Soon a white solid started to separate. The suspension was stirred at ambient temperature for 15 hours, then the solid was filtered off, washed with methanol (3.x.5 mL) and anhydrous ether (2.x.5 mL), then dried in vacuum. The crude 5-azacytidine (4.5 g, 41.3percent) was further purified from DMSO and methanol (for details see Example 4).
Reference: [1] Patent: US2004/186283, 2004, A1. Location in patent: Page 8
[2] Patent: US2004/186283, 2004, A1. Location in patent: Page 8
  • 3
  • [ 10302-78-0 ]
  • [ 320-67-2 ]
YieldReaction ConditionsOperation in experiment
75% at 20 - 25℃; for 1.58 h; [00122] The latter was dissolved in MeOH (240 g) and the resulting mixture was filtered (small amount of salt).[00123] 25percent MeONaMeOH (15.4 g; 0.02 mol) dissolved in MeOH (250 g) was added over 5 min.[00124] The resulting mixture is stirred at 20-25°C for 1.5 h. The crystals were filtered and washed with MeOH (300 g).[00125] The wet solid was dried under vacuum at 60°C for 15 h to give 5-azacytidine as an off white solid.[00126] Yield: 75percent, purity >99percent area by HPLC.
400 g With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 20 - 25℃; for 6.00 h; To a solution of 2,3,5-tri-O-acetyl-β-D-ribofuranose-4-amino-1,3,5-triazine (1.0 Kg) which is dissolved in DBU (5.0 L) was added methanol (40 L) and stirred for 6 h at 20-25 °C. Filtered the solid and washed with methanol (500 mL) and suck dried for 30 min and subjected for drying under vacuum tray drier to get crude 400 g of 4-amino-1-β-D-ribofuranosyl-s-triazin-2(1H)-one.
Reference: [1] Patent: WO2010/17374, 2010, A1. Location in patent: Page/Page column 18
[2] Patent: WO2010/14883, 2010, A2. Location in patent: Page/Page column 26
[3] Patent: WO2012/135405, 2012, A1. Location in patent: Page/Page column 66
[4] Asian Journal of Chemistry, 2018, vol. 30, # 7, p. 1521 - 1524
  • 4
  • [ 931-86-2 ]
  • [ 14215-97-5 ]
  • [ 320-67-2 ]
Reference: [1] Patent: EP2371825, 2011, A1. Location in patent: Page/Page column 9
[2] Patent: US2011/245485, 2011, A1. Location in patent: Page/Page column 6
  • 5
  • [ 931-86-2 ]
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  • [ 320-67-2 ]
Reference: [1] Patent: EP2371825, 2011, A1. Location in patent: Page/Page column 9
[2] Patent: US2011/245485, 2011, A1. Location in patent: Page/Page column 6
  • 6
  • [ 56787-28-1 ]
  • [ 320-67-2 ]
Reference: [1] Organic Process Research and Development, 2013, vol. 17, # 2, p. 303 - 306
  • 7
  • [ 28998-36-9 ]
  • [ 320-67-2 ]
Reference: [1] Pharmaceutical Chemistry Journal, 2016, vol. 49, # 12, p. 804 - 809
  • 8
  • [ 52523-35-0 ]
  • [ 13035-61-5 ]
  • [ 320-67-2 ]
Reference: [1] Patent: WO2009/16617, 2009, A2. Location in patent: Page/Page column 15-16
  • 9
  • [ 65126-88-7 ]
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Reference: [1] Journal of Pharmaceutical Sciences, 1981, vol. 70, # 11, p. 1228 - 1232
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