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2-[(3,3,3-trifluoropropyl)thio]-6-amino-9h-purine and its preparation method

A technology of trifluoropropyl and amino, which is applied in the field of 2-[(3,3,3-trifluoropropyl)thio]-6-amino-9H-purine and its preparation method, and can solve the danger of enlarged production , labor protection and equipment requirements, flammable and explosive, etc.

Active Publication Date: 2020-04-24
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] In summary, the disclosed preparation method of the key intermediate of cangrelor (1) requires highly toxic, flammable and explosive reagents, high labor protection and equipment requirements, and strong risk of scale-up production

Method used

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  • 2-[(3,3,3-trifluoropropyl)thio]-6-amino-9h-purine and its preparation method
  • 2-[(3,3,3-trifluoropropyl)thio]-6-amino-9h-purine and its preparation method
  • 2-[(3,3,3-trifluoropropyl)thio]-6-amino-9h-purine and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0112] Preparation of 4,6-diamino-2-mercaptopyrimidine (4)

[0113]

[0114] Sodium ethoxide (358g, 5.26mol) was added to 2L of ethanol, followed by thiourea (200g, 2.63mol) and malononitrile (226g, 3.42mol), and stirred at 85°C for 12h. Cool down to room temperature, filter, and dissolve the filter cake with 3 L of water, adjust the pH to 7 with acetic acid, filter, and dry to obtain 336 g of a light yellow solid, with a yield of 90%.

[0115] ESI-MS(m / z):143.03[M+H] + ;

[0116] 1 HNMR (400MHz, DMSO-d 6 )δ: 11.14(s,1H),6.71(s,4H),5.05(s,1H).

Embodiment 2

[0118] Preparation of 4,6-diamino-2-mercaptopyrimidine (4)

[0119] Sodium methoxide (213g, 3.94mol) was added to 1L methanol, thiourea (100g, 1.31mol) and malononitrile (200g, 3.02mol) were added in turn, and stirred at 70°C for 9h. Cool down to room temperature, filter, dissolve the filter cake with 1.5 L of water, adjust the pH to 7 with acetic acid, filter, and dry to obtain 166 g of light yellow solid with a yield of 89%.

Embodiment 3

[0121] Preparation of 4,6-diamino-2-mercaptopyrimidine (4)

[0122] Potassium tert-butoxide (147g, 1.31mol) was added to 1L tert-butanol, followed by thiourea (100g, 1.31mol) and malononitrile (86.8g, 1.31mol), and stirred at 60°C for 24h. Cool down to room temperature, filter, and dissolve the filter cake with 1.7 L of water, adjust the pH to 7 with acetic acid, filter, and dry to obtain 174 g of light yellow solid with a yield of 93%.

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Abstract

The invention discloses 2-[(3,3,3-trifluoropropyl)thio]-6-amino-9H-purine and a preparation method thereof. 2-[(3,3,3-trifluoropropyl)thio]-6-amino-9H-purine can be used for preparation of 6-N-[2-(methylthio)ethyl]-2-[(3,3,3-trifluoropropyl)thio]adenosine. The preparation method provided by the invention is simple in operation, mild in reaction conditions, easy in purification of intermediates and high in the yield of reactions in every step, avoids defects and insufficiencies in reported preparation methods for the key cangrelor intermediate 6-N-[2-(methylthio)ethyl]-2-[(3,3,3-trifluoropropyl)thio]adenosine, and is suitable for industrial production. The structural formula of 2-[(3,3,3-trifluoropropyl)thio]-6-amino-9H-purine is as described in the specification.

Description

technical field [0001] The invention relates to a substituted purine compound and its preparation method and application. Background technique [0002] Cangrelor tetrasodium was developed by AstraZeneca in the United Kingdom, and after ten years of clinical research by Medicines in the United States, it was approved for marketing by the European Union on March 23, 2015, and approved by the FDA on June 22, 2015 It is marketed for patients receiving percutaneous coronary intervention (PCI), aiming to reduce the incidence of adverse events such as perioperative myocardial infarction, repeated revascularization, and stent thrombosis. The trade name is Kengreal. Cangrelor is an intravenous platelet P2Y 12 As a receptor reversible inhibitor, compared with clopidogrel, which is widely used clinically, and similar drugs already on the market, cangrelor has the advantages of good curative effect, short onset and failure time, flexible medication, and wide application range. [0003...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D473/24C07H19/167C07H1/00
CPCC07D473/24C07H1/00C07H19/167
Inventor 李建其鲁宽莹马志龙金勋奇刘彪
Owner SHANGHAI INST OF PHARMA IND CO LTD