GB735702A - Improvements in and relating to 2,4-diaminopyrimidines and methods of making the same - Google Patents

Improvements in and relating to 2,4-diaminopyrimidines and methods of making the same

Info

Publication number
GB735702A
GB735702A GB694452A GB694452A GB735702A GB 735702 A GB735702 A GB 735702A GB 694452 A GB694452 A GB 694452A GB 694452 A GB694452 A GB 694452A GB 735702 A GB735702 A GB 735702A
Authority
GB
United Kingdom
Prior art keywords
thienyl
diamino
give
prepared
guanidine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB694452A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB694452A priority Critical patent/GB735702A/en
Publication of GB735702A publication Critical patent/GB735702A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Abstract

Compounds of the formula <FORM:0735702/IV (b)/1> wherein R is an alkyl radical of 1 to 3 carbon atoms and Ar is a thienyl, furyl, quinolyl or thiazyl radical, are prepared by reacting a b -alkoxyacrylonitrile of the formula <FORM:0735702/IV (b)/2> wherein R1 is a lower alkyl radical, with guanidine. The radical Ar may be substituted with chlorine, bromine or nitro groups by chlorinating, brominating or nitrating the product. In the examples: (1) the reaction product of 2-furylacetonitrile, ethyl acetate and sodium is neutralized and treated with diazomethane and the resulting substituted-nitrile is reacted with guanidine to give 2,4-diamino-5-(2-furyl)-6-methyl pyrimidine which forms a hydrochloride salt; (2) a -acetyl-2-thienylacetonitrile, prepared from 2-thienylacetonitrile, ethyl acetate and sodium ethoxide, is treated with diazomethane and the product is refluxed with guanidine to give 2,4-diamino-5-(2-thienyl)-6-methyl pyrimidine; (3) the pyrimidine of example 2 is brominated; (4) 2,4-diamino-5-(2-thienyl)-6-ethyl pyrimidine is prepared in a similar manner to example 2 using ethyl propionate instead of ethyl acetate; (5) the compound of example 4 is brominated to give a mixture of the bromo-2-thienyl and the dibromo-2-thienyl derivatives; (6) 2,4-diamino-5-(2-thienyl)-6-isopropylpyrimidine is prepared as in example 4 using methyl isobutyrate instead of ethyl propionate; (7) and (8) the compound of example 6 is brominated to give the bromo- and dibromo-2-thienyl derivatives; (9) and (10) the compound of example 2 is chlorinated to give the dichloro- and monochloro-2-thienyl derivatives; (11) the compound of example 1 is brominated to give 2,4-diamino-5-(bromo-2-furyl) - 6 - methylpyrimidine; (12) 2,4-diamino - 5 - (2 - quinolyl) - 6 - methylpyrimidine is prepared from a - acetyl - 2 - quinolylacetonitrile, diazomethane and guanidine, and forms a hydrochloride; (13) 2,4-diamino-5-(2-thienyl)-6-methylpyrimidine is nitrated with potassium nitrate in conc. sulphuric acid; (14) a - acetyl - 2 - phenylthiazolyl - (4) - acetonitrile, prepared from 2 - phenylthiazolyl - (4) - acetonitrile, ethyl acetate and sodium ethoxide, is reacted with diazomethane and then with guanidine to give 2,4 - diamino - 5 - (2 - phenylthiazolyl - 4) - 6 - methylpyrimidine. Specification 715,813 is referred to.
GB694452A 1952-03-18 1952-03-18 Improvements in and relating to 2,4-diaminopyrimidines and methods of making the same Expired GB735702A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB694452A GB735702A (en) 1952-03-18 1952-03-18 Improvements in and relating to 2,4-diaminopyrimidines and methods of making the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB694452A GB735702A (en) 1952-03-18 1952-03-18 Improvements in and relating to 2,4-diaminopyrimidines and methods of making the same

Publications (1)

Publication Number Publication Date
GB735702A true GB735702A (en) 1955-08-24

Family

ID=9823707

Family Applications (1)

Application Number Title Priority Date Filing Date
GB694452A Expired GB735702A (en) 1952-03-18 1952-03-18 Improvements in and relating to 2,4-diaminopyrimidines and methods of making the same

Country Status (1)

Country Link
GB (1) GB735702A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3001909A (en) * 1957-09-12 1961-09-26 Merck & Co Inc Coccidiosis control composition
EP0233461A2 (en) * 1986-01-13 1987-08-26 American Cyanamid Company 4,5,6-Substituted-2-pyrimidinamines
JP2015129153A (en) * 2008-08-20 2015-07-16 メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． Substituted pyridine and pyrimidine derivatives and their use in treating viral infections
WO2021214494A1 (en) 2020-04-24 2021-10-28 University Of Greenwich Interleukin inhibitors

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3001909A (en) * 1957-09-12 1961-09-26 Merck & Co Inc Coccidiosis control composition
EP0233461A2 (en) * 1986-01-13 1987-08-26 American Cyanamid Company 4,5,6-Substituted-2-pyrimidinamines
EP0233461A3 (en) * 1986-01-13 1988-05-25 American Cyanamid Company 4,5,6-substituted-2-pyrimidinamines
JP2015129153A (en) * 2008-08-20 2015-07-16 メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． Substituted pyridine and pyrimidine derivatives and their use in treating viral infections
WO2021214494A1 (en) 2020-04-24 2021-10-28 University Of Greenwich Interleukin inhibitors

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