GB475559A - Process for the manufacture of pyramidine compounds - Google Patents

Process for the manufacture of pyramidine compounds

Info

Publication number
GB475559A
GB475559A GB1420036A GB1420036A GB475559A GB 475559 A GB475559 A GB 475559A GB 1420036 A GB1420036 A GB 1420036A GB 1420036 A GB1420036 A GB 1420036A GB 475559 A GB475559 A GB 475559A
Authority
GB
United Kingdom
Prior art keywords
group
amino
yield
methyl
ester
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
GB1420036A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB1420036A priority Critical patent/GB475559A/en
Publication of GB475559A publication Critical patent/GB475559A/en
Expired legal-status Critical Current

Links

Abstract

2-Alkyl-(or 2-aralkyl)-4-amino-5-aminoalkylpyrimidines are prepared as follows. An amidine of an aliphatic or araliphatic carboxylic acid is condensed with an acetonitrile derivative substituted by (a) a hydroxymethylene group, an etherified hydroxymethylene group, or a carboxylic ester group, and (b) a protected aminoalkyl group or a group (as defined below) convertible into an aminoalkyl group. When substituent (a) is a hydroxymethylene or an etherified hydroxymethylene group, the reaction yields a 2 - alkyl - (or 2 - aralkyl) - 4 - aminopyrimidine substituted in the 5-position with a substituent as at (b) above, and this product is treated to convert the substituent in the 5-position into an aminoalkyl group. When substituent (a) is a carboxylic ester group, the reaction yields a 2-alkyl-(or 2-aralkyl)-4-amino-6-hydroxypyrimidine (or the corresponding tautomeric 6-oxo compound) substituted in the 5-position with a substituent as at (b) above; this product is treated to replace the substituent in the 6-position successively by halogen and hydrogen, e.g. by the successive action of a phosphorus halide and a reducing agent such as zinc dust, and the substituent in the 5-position is then treated to convert it into an aminoalkyl group. The substituent as at (b) above may be an acylaminoalkyl group or any of the following: a carboxylic acid ester or amide group, an alkylcarboxylic acid or ester group, a cyano or cyanoalkyl group, or an alkoxyalkyl group. An alkylcarboxylic acid or ester group may be converted into an aminoalkyl group by way of the alkylcarboxylic amide or hydrazide group, which may then be degraded in known manner, e.g. by the Hoffmann or Curtius reaction. A carboxylic ester group may be converted into an aminoalkyl group by way of the carboxylic amide group, which is converted into a cyano group and then reduced. A cyanoalkyl group is converted into an aminoalkyl group by reduction. An alkoxyalkyl group may be converted into an aminoalkyl group by way of a halogenalkyl group. In the examples: (1) acetamidine hydrochloride and cyanosuccinic acid diethyl ester yield 2 - methyl - 4 - amino - 6 - hydroxypyrimidine-5-acetic ester, which is treated successively with phosphorus oxychloride and zinc dust to yield 2-methyl-4-aminopyrimidine-5-acetic ester; the latter is treated with ammonia in methyl alcohol to yield 2-methyl-4-aminopyrimidine-5-acetamide, which is converted into 2-methyl-4-amino-5-aminomethylpyrimidine as described in Specification 473,193; (2) acetamidine hydrochloride and ethoxymethylenemalonic acid dinitrile yield 2-methyl-4-amino-5-cyanopyrimidine, which is hydrogenated to yield 2-methyl-4-amino-5-aminomethylpyrimidine; if propionamidine is used in place of acetamidine, 2-ethyl-4-amino-5-cyano-and 2-ethyl-4-amino-5-aminomethyl-pyrimidine are obtained; (3) phenylacetamidine hydrochloride and cyanosuccinic acid diethyl ester yield 2-benzyl-4-amino-6-hydroxypyrimidine-5-acetic ester, which is treated with phosphorus oxychloride to yield 2-benzyl-4-amino-6-chloropyrimidine-5-acetic ester; the latter, by treatment with zinc dust, yields 2-benzyl-4-aminopyrimidine-5-acetic ester, from which, by treatment with ammonia in methyl alcohol, 2-benzyl-4-aminopyrimidine-5-acetamide is obtained, and is converted into 2-benzyl-4-amino-5-aminomethylpyrimidine as described in Specification 473,193; (4) phenylacetamidine hydrochloride and ethoxymethylenemalonic acid dinitrile yield 2-benzyl-4-amino-5-cyanopyrimidine, which is hydrogenated to yield 2-benzyl-4-amino-5-aminomethylpyrimidine; (5) cyanacetic ester is treated with bromoethylphthalimide to yield phthalimidoethyl-cyanacetic ester, and the latter is condensed with acetamidine hydrochloride to yield 2-methyl-4-amino - 5 - phthalimidoethyl - 6 - hydroxypyrimidine; the latter, by treatment with phosphorus oxychloride, yields 2-methyl-4-amino-5-phthalimidoethyl-6-chloropyrimidine, which is treated successively with hydrazine hydrate and hydrochloric acid to yield 2-methyl-4-amino-5-aminoethyl-6-hydrazinopyrimidine; the latter, by treatment with copper sulphate in sulphuric acid solution, yields 2-methyl-4-amino-5-aminoethylpyrimidine.
GB1420036A 1936-05-19 1936-05-19 Process for the manufacture of pyramidine compounds Expired GB475559A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1420036A GB475559A (en) 1936-05-19 1936-05-19 Process for the manufacture of pyramidine compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1420036A GB475559A (en) 1936-05-19 1936-05-19 Process for the manufacture of pyramidine compounds

Publications (1)

Publication Number Publication Date
GB475559A true GB475559A (en) 1937-11-19

Family

ID=10036857

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1420036A Expired GB475559A (en) 1936-05-19 1936-05-19 Process for the manufacture of pyramidine compounds

Country Status (1)

Country Link
GB (1) GB475559A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2820050A (en) * 1955-07-22 1958-01-14 American Cyanamid Co Substituted propionitriles and preparation of the same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2820050A (en) * 1955-07-22 1958-01-14 American Cyanamid Co Substituted propionitriles and preparation of the same

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