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[ CAS No. 104227-86-3 ] {[proInfo.proName]}

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Chemical Structure| 104227-86-3
Chemical Structure| 104227-86-3
Structure of 104227-86-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 104227-86-3 ]

CAS No. :104227-86-3 MDL No. :MFCD00870146
Formula : C10H15N5O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 237.26 Pubchem ID :-
Synonyms :

Safety of [ 104227-86-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 104227-86-3 ]

* 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 [ 104227-86-3 ]
  • Downstream synthetic route of [ 104227-86-3 ]

[ 104227-86-3 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 108-24-7 ]
  • [ 104227-86-3 ]
  • [ 104227-87-4 ]
YieldReaction ConditionsOperation in experiment
90% With triethylamine In dichloromethane at 20 - 30℃; for 10 h; To a dry 1 L flask were added the intermediate diol 5 (50 g, 21.5 mmol), dichloromethane (500 ml), triethylamine (31 g, 30.6 mmol) and catalytic dimethylaminopyridine (3.1 g). The acetic anhydride (120 g, 31 mmol) was then added dropwise, keeping the solution at 2530° C. The reaction mixture was stirred at room temperature for 10 hours. Water was added to dilute the reaction mixture, and 5percent Sodium hydroxyl solution (5percent) was added till the solution turned neutral. The separated organic layer was washed with water (200 ml.x.2), saturated brine and dried by sodium sulphate. The dichloromethane was then removed under reduced pressure, and residue was dissolved with boiling methanol (180 ml). The famciclovir crystallized out by keeping the methanol solution at 04° C. for 4 hours (60 g, yield 90percent).
Reference: [1] Synthesis, 2004, # 12, p. 2026 - 2034
[2] Patent: US2006/264629, 2006, A1, . Location in patent: Page/Page column 4; 5
[3] Nucleosides and Nucleotides, 1996, vol. 15, # 5, p. 981 - 994
[4] Patent: WO2008/72074, 2008, A1, . Location in patent: Page/Page column 12; 13; 13-14
[5] Heterocycles, 2008, vol. 75, # 11, p. 2803 - 2808
  • 2
  • [ 104227-86-3 ]
  • [ 104227-87-4 ]
YieldReaction ConditionsOperation in experiment
91% With pyridine; dmap; acetic anhydride In tetrahydrofuran; methanol c)
9-(4-Acetoxy-3-acetoxymethylbut-1-yl)-2-aminopurine STR34
To a suspension of 2-amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine (0.13 g, 0.55 mmol) in dry tetrahydrofuran (40 ml), stirred at room temperature under dry nitrogen were added pyridine (117 μl, 1.45 mmol) and 4-dimethylaminopyridine (5 mg, 41 μmol) followed by acetic anhydride (108 μl, 1.14 mmol).
The mixture was stirred at room temperature for 5 h. giving a clear, colourless solution. T.1.c. [chloroform/methanol (9:1)] showed the major product to be the title compound, rf=0.40.
Methanol (5 ml) was added, the mixture stirred for 5 mins.
then evaporated to dryness.
The residue was partitioned between water (5 ml) and chloroform (10 ml).
The aqueous portion was extracted with chloroform (4*10 ml) then the combined organic portions dried over magnesium sulphate, filtered and evaporated to leave a pale yellow glassy material which was column chromatographed on silica (20 g) [eluant=chloroform/methanol (19:1)] to give the title compound (0.16 g, 91percent) as a colourless viscous oil, which was crystallized from n-butanol (0.6 ml) to give colourless crystals (118 mg., 67percent), m.p. 102° C.
1 H n.m.r(CDCl3) 61.90(m,3H,--CH2 --+>CH--), 2.00(s,6H,--CH3), 4.05(d,4H,3 JHH =5 Hz,--CH2 --O), 4.10(t,2H,3 JHH =6 Hz,>NCH2 --), 5.35(br.s,2H,--NH2), 7.70(s,1H,H-8), 8.60(s,1H,H-6).
Reference: [1] Patent: US5175288, 1992, A,
  • 3
  • [ 97845-60-8 ]
  • [ 104227-87-4 ]
  • [ 104227-86-3 ]
  • [ 120687-07-2 ]
YieldReaction ConditionsOperation in experiment
64% With ammonium formate In methanol; acetic acid methyl ester at 40℃; for 6.16667 h; Into a jacketed reactor equipped with a mechanical stirrer, a reflux condenser and a thermocouple, under an inert atmosphere (N2), was added dry 7 percent Pd/C (3.48 g), MeOAc (500 ml), MEOH (50 ml), Cl-FMC (50.1 g; 49.6 mmol), and ammonium formate (27. 18 g; 97 percent pure). The reaction mixture was heated at 40°C for 6 hours and 10 min. At this stage 98. 37 percent FMC, 0.82 percent MH-FMC and 0.63 percent DH-FMC and 0.18 percent Cl- FMC; were detected. Upon cooling the reaction mixture and filtering the black solid, the filtrate was evaporated to dryness leaving 43.77 g solid (almost the entire expected amount of FMC; assay 97.3 percent FMC). The composition of the solid was left unchanged from the above quotation. The solid was partitioned in EtOAc (365 ml) and water (150 ml). The organic phase was washed with H20 (45 ml), and kept aside. The combined aqueous phases were washed with EtOAc (3 x 40 ml). The combined EtOAc extracts were washed with H20 (40 ml), and kept aside. The aqueous phases were extracted again with EtOAc (2 x 40 ml). The EtOAc extracts were washed with HA0 (10 ml), and kept aside. The three organic phases were combined, dried with MGS04 and evaporated to dryness leaving 34.7 g white solid (-76. 8 percent yield). The solid was crystallized in BUOH (100 ml; 63°C) giving 28.9 g pure FMC (64 percent yield). Less then 0.1 percent impurities (each) were detected in the crystals.
Reference: [1] Patent: WO2004/99208, 2004, A1, . Location in patent: Page 6-7
[2] Patent: WO2004/99208, 2004, A1, . Location in patent: Page 6-7
[3] Patent: WO2004/99208, 2004, A1, . Location in patent: Page 8
[4] Patent: WO2004/99208, 2004, A1, . Location in patent: Page 7-8
[5] Patent: WO2004/99208, 2004, A1, . Location in patent: Page 8-9
[6] Patent: WO2004/99208, 2004, A1, . Location in patent: Page 9
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