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9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropuine

1,3-Propanediol,2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]diacetate(ester)

CAS: 97845-60-8

Molecular Formula: C14H18ClN5O4

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9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropuine - Names and Identifiers

Name 1,3-Propanediol,2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]diacetate(ester)
Synonyms 9-(4-Acetoxy-3-aceto
intermediate of Famciclover
9-[4-Acetoxy-3-(acetoxymethyl)butyl]-2-amino-6-chl
9-(4-ACETOXY-3)-ACETOXYMETHYLBURYL-2-AMINO-6-CHLOROPURINE
9-(4-Acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine
9-(4-ACETOXY-3-ACETOXYMETHYLBUT-1-YL)-2-AMINO-6-CHLOROPUINE
9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropuine
9-(4-ACETOXY-3-ACETOXYMETHYLBUT-1-YL)-2-AMINO-6-CHLOROPURINE
9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropurine
2-(2-(2-AMino-6-chloro-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate
2-[(acetyloxy)methyl]-4-(2-amino-6-chloro-9H-purin-9-yl)butyl acetate
1,3-Propanediol,2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]diacetate(ester)
1,3-Propanediol,2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]diacetate(ester)(9Cl
CAS 97845-60-8
EINECS 619-293-7
InChI InChI=1/C14H18ClN5O4/c1-8(21)23-5-10(6-24-9(2)22)3-4-20-7-17-11-12(15)18-14(16)19-13(11)20/h7,10H,3-6H2,1-2H3,(H2,16,18,19)

9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropuine - Physico-chemical Properties

Molecular FormulaC14H18ClN5O4
Molar Mass355.78
Density1.49±0.1 g/cm3(Predicted)
Melting Point132-134 °C(Solv: isopropanol (67-63-0))
Boling Point575.0±60.0 °C(Predicted)
Flash Point301.536°C
Solubility DMSO (Slightly), Methanol (Slightly)
Vapor Presure0Pa at 25℃
AppearanceSolid
ColorOff-White to Light Yellow
pKa2.23±0.10(Predicted)
Storage Conditionunder inert gas (nitrogen or Argon) at 2–8 °C
Refractive Index1.64
Physical and Chemical PropertiesAppearance: yellowish to off-white crystals

9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropuine - Reference Information

LogP0.92 at 25℃ and pH9.1
Introduction 9-(4-acetoxy-3-acetoxymethylbutyl) 2-amino-6-chloropurine is a key intermediate for the preparation of famciclovir and penciclovir. Penciclovir and famciclovir are the British Smith Kline

Beecham 20 actual 90 years of development of anti-Virus drugs, mainly through the inhibition of Virus DNA replication to play an anti-Virus effect, it is indicated for the treatment of Virus infections such as severe herpes zoster and primary genital herpes.
preparation (1) put 1, 3-dichloro-2-propanol 129g, DMF
53.5 ml, potassium acetate 300g, ammonium chloride 100g, stirred at 110 ~ deg C between the heat preservation reaction for 10 hours. After heat preservation and cooling to room temperature, the solid in the system is filtered off, the filtrate is concentrated under reduced pressure to DMF, and 1000mL of ethyl acetate is added to dissolve the concentrated solution, which is washed twice with water and dried over anhydrous sodium sulfate, add triethylamine hydrobromide

270g, raise the temperature to 70~80 ℃, stir and keep the reaction for 5~6 hours, cool to room temperature, filter the solid in the system, then, the mixture was washed twice with a saturated sodium chloride solution, and the ethyl acetate was concentrated under reduced pressure and subjected to distillation to obtain 110g of 1, 3-diacetoxy-2-bromopropane with a GC content of 90.4%. (2) add THF
100ml, 9g of Anhydrous Lithium bromide and 33g of zinc powder to the reaction bottle, replace with nitrogen for 3 times, and then add 100g of 1, 3-diacetoxy-2-bromopropane, finally, add 2.3gTMSCl (trimethylchlorosilane)
, heat to 50 ℃, react at 50~55 ℃ for 1~3H, then heat to 60~65 ℃, reaction at this temperature
15~24H, GC detection, to 1, 3-diacetoxy-2-bromopropane/1,3-diacetoxy-2-
zinc bromide propane <5% when the end of the reaction, zinc reagent (1, 3-diacetoxy-2-zinc bromide propane), pending use. (3) in the reaction flask, 5ml of THF was added, and nitrogen was substituted for 3 times. At room temperature, S-Phos g of palladium acetate and 1.1g of (2-dicyclohexylphosphine-2 ',6'-dimethoxybiphenyl) were added, under the protection of nitrogen, the catalyst was obtained by stirring for 20-30 minutes and was ready for use. (4) Add 375ml of tetrahydrofuran and 75g of 2-amino-6-chloro-9-bromoethylpurine to the reaction flask, and add the newly prepared catalyst under the protection of nitrogen, after heating to 50~60 ℃, the newly prepared zinc reagent was slowly added dropwise, and the reaction was carried out at 50~60 ℃ for 10H. The temperature was lowered to 15~20 ℃, and 10ml of ethanol was added dropwise and stirred for 2H. Concentrate to dryness under reduced pressure, add methylene chloride 500ml, water 300ml and glacial acetic acid 50ml, stir for 20~30 minutes, separate layers, wash organic layer with sodium bicarbonate solution 2 times, then wash with water 2 times, concentrate to dryness, the concentrate was recrystallized from ethanol and dried under reduced pressure to obtain about 80g of 9-(4-acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine, HPLC purity of more than 99.5%.
Last Update：2024-04-09 21:32:09
9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropuine
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Product Name: 9-(4-Acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine Request for quotation
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Tel: 86-10-10086 81625225
Email: yeqim@boyechemicals.com
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SHANGHAI ACMEC BIOCHEMICAL TECHNOLOGY CO., LTD.
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Product Name: 9-(4-ACETOXY-3-ACETOXYMETHYLBUTYL)-2-AMINO-6-CHLOROPURINE Visit Supplier Webpage Request for quotation
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Shanghai Macklin Biochemical Co., Ltd
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Product Name: 2-(2-(2-Amino-6-chloro-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate Visit Supplier Webpage Request for quotation
CAS: 97845-60-8
Tel: +86-18821248368
Email: Int06@meryer.com
Mobile: +86-18821248368
QQ: 495145328 Click to send a QQ message
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Shanghai Yuanye Bio-Technology Co., Ltd.
Product Name: 9-[4-Acetoxy-3-(acetoxymethyl)butyl]-2-amino-6-chloropurine Visit Supplier Webpage Request for quotation
CAS: 97845-60-8
Tel: 18301782025
Email: 3008007409@qq.com
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View History
9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropuine
4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2YL) PHE
765-12-8
1195-67-1
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