GB699812A - Manufacture of substituted pyrimidones - Google Patents
Manufacture of substituted pyrimidonesInfo
- Publication number
- GB699812A GB699812A GB2915850A GB2915850A GB699812A GB 699812 A GB699812 A GB 699812A GB 2915850 A GB2915850 A GB 2915850A GB 2915850 A GB2915850 A GB 2915850A GB 699812 A GB699812 A GB 699812A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrimidone
- diketene
- methyl
- dimethyl
- phenyl
- 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
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Substituted pyrimidones of the general formula <FORM:0699812/IV (b)/1> (wherein R represents hydrogen or an alkyl or aryl radical, X an alkyl, aryl, -NHR1 or -SR2 group, R1 hydrogen or an alkyl radical and R2 an alkyl radical) are manufactured by reacting diketene with an amidine, guanidine or isothiourea of the general formula <FORM:0699812/IV (b)/2> or with a salt thereof if the reaction be effected in the presence of an alkaline material. The reaction is desirably carried out in a diluent medium, which should be a solvent for the second reactant, such as water, an organic solvent (e.g. an alcohol, ether, ester, ketone, aromatic hydrocarbon, or chlorinated hydrocarbon), or an aqueous organic solvent, and may take place at temperatures in the range -10 DEG to 60 DEG C. (e.g. at room temperature). When X represents -SR2, the product may be hydrolysed to the corresponding uracil and mercaptan. In examples: (1) and (2) diketene is shaken with benzamidine hydrochloride in aqueous caustic soda or with benzamidine in water to produce 2-phenyl-4-methyl-6-pyrimidone; (3) diketene is stirred with guanidine carbonate in aqueous caustic soda to yield 2-amino-4-methyl-6-pyrimidone; (4) the same product is obtained by reacting guanidine hydrochloride as in (1); (5) S-methylisothiouronium iodide (from thiourea and methyl iodide) similarly yields 2-methylmercapto-4-methyl-6-pyrimidone; (6) diketene is stirred with acetamidine hydrochloride in ethanol in the presence of sodium ethoxide to form 2 : 4-dimethyl-6-pyrimidone; (7) to (9) diketene is stirred with N-phenyl-S-methylisothiourea in ethanol, ether, chloroform, acetone, dioxan, benzene or ethyl acetate, and an intermediate product which is formed is converted with alkali to 2-methylmercapto-1-phenyl-4-methyl-6-pyrimidone; (10) diketene is stirred with N : S-dimethylisothiouronium iodide in aqueous caustic soda to given 2-methylmercapto-1 : 4-dimethyl-6-pyrimidone; (11) diketene is allowed to stand with methylguanidine hydrochloride in aqueous caustic soda to produce 1 : 4-dimethyl-2-amino-6-pyrimidone; (12) a solution of sodium in ethanol is added to a solution of methylbenzamidine hydrochloride in ethanol, the precipitated sodium chloride is removed, diketene is added and the solution allowed to stand, producing 1 : 4-dimethyl-2-phenyl-6-pyrimidone. Other starting materials specified are propionamidine, phenylacetamidine (R = H, X = C6H5CH2-), N : N1 - dimethyl - guanidine, phenylguanidine, N - methyl - N1 - phenylguanidine, S - ethylisothiourea and N - phenyl- and N-methyl-S-ethylisothiourea.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2915850A GB699812A (en) | 1950-11-29 | 1950-11-29 | Manufacture of substituted pyrimidones |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2915850A GB699812A (en) | 1950-11-29 | 1950-11-29 | Manufacture of substituted pyrimidones |
Publications (1)
Publication Number | Publication Date |
---|---|
GB699812A true GB699812A (en) | 1953-11-18 |
Family
ID=10287051
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2915850A Expired GB699812A (en) | 1950-11-29 | 1950-11-29 | Manufacture of substituted pyrimidones |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB699812A (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2931887A1 (en) * | 1978-08-08 | 1980-02-21 | Ciba Geigy Ag | METHOD FOR PRODUCING 2-ALKYL OR CYCLOALKYL-4-METHYL-6-HYDROXYPYRIMIDINES |
EP1506967A1 (en) * | 2003-08-13 | 2005-02-16 | Syrrx, Inc. | Dipeptidyl peptidase inhibitors |
EP1911754A1 (en) * | 2003-08-13 | 2008-04-16 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
US7807689B2 (en) | 2004-03-15 | 2010-10-05 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
US8084605B2 (en) | 2006-11-29 | 2011-12-27 | Kelly Ron C | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
US8093236B2 (en) | 2007-03-13 | 2012-01-10 | Takeda Pharmaceuticals Company Limited | Weekly administration of dipeptidyl peptidase inhibitors |
US8222411B2 (en) | 2005-09-16 | 2012-07-17 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
US8324383B2 (en) | 2006-09-13 | 2012-12-04 | Takeda Pharmaceutical Company Limited | Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile |
US8906901B2 (en) | 2005-09-14 | 2014-12-09 | Takeda Pharmaceutical Company Limited | Administration of dipeptidyl peptidase inhibitors |
-
1950
- 1950-11-29 GB GB2915850A patent/GB699812A/en not_active Expired
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2931887A1 (en) * | 1978-08-08 | 1980-02-21 | Ciba Geigy Ag | METHOD FOR PRODUCING 2-ALKYL OR CYCLOALKYL-4-METHYL-6-HYDROXYPYRIMIDINES |
EP1506967A1 (en) * | 2003-08-13 | 2005-02-16 | Syrrx, Inc. | Dipeptidyl peptidase inhibitors |
WO2005016911A1 (en) * | 2003-08-13 | 2005-02-24 | Takeda Pharmaceutical Company Limited | 4-pyrimidone derivatives and their use as peptidyl peptidase inhibitors |
JP2005060401A (en) * | 2003-08-13 | 2005-03-10 | Syrrx Inc | Dipeptidyl peptidase inhibitor |
EP1911754A1 (en) * | 2003-08-13 | 2008-04-16 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
US7807689B2 (en) | 2004-03-15 | 2010-10-05 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
US8906901B2 (en) | 2005-09-14 | 2014-12-09 | Takeda Pharmaceutical Company Limited | Administration of dipeptidyl peptidase inhibitors |
US8222411B2 (en) | 2005-09-16 | 2012-07-17 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
US8324383B2 (en) | 2006-09-13 | 2012-12-04 | Takeda Pharmaceutical Company Limited | Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile |
US8084605B2 (en) | 2006-11-29 | 2011-12-27 | Kelly Ron C | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
US8093236B2 (en) | 2007-03-13 | 2012-01-10 | Takeda Pharmaceuticals Company Limited | Weekly administration of dipeptidyl peptidase inhibitors |
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