83655-13-4

Basic information

• Product Name: 2-Pyrimidinamine, N,4-dimethyl-6-phenyl-
• CAS NO: 83655-13-4
• Molecular Formula: C12H13N3
• Molecular Weight: 199.255
• Mol File: 83655-13-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-Pyrimidinamine, N,4-dimethyl-6-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyrimidinamine, N,4-dimethyl-6-phenyl-(83655-13-4)
• EPA Substance Registry System: 2-Pyrimidinamine, N,4-dimethyl-6-phenyl-(83655-13-4)

Safety Data

• Hazardous Substances Data: 83655-13-4(Hazardous Substances Data)

Upstream product

• 471-29-4 1-methylguanidine 
• 93-91-4 1-phenylbutan-1,3-dione 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 83655-36-1 1,4-methyl-6-phenyl-2(1H)-pyrimidinethione 

Downstream Products

• 89242-68-2 N²,4-Dimethyl-6-phenyl-2-pyrimidinamin*Picrat 

Relevant articles and documents

Dihydropyrimidines and Related Structures. I. N2-Substituted 2-Pyrimidinamines and Dihydro-2-pyrimidinamines by Reaction of Phenylbutenones and Monosubstituted Guanidines

The reactions of monosubstituted guanidines 2 with phenylbutenones 7 and 10 exclusively yield N2-substituted 2-pyrimidinamines 8 and 9.The structure of the reaction products is proved and their differing stability is discussed.Action of methyl- and benzylguanidine respectively (2b,c) on 4-phenyl-3-buten-2-one (7) and of 2c on 1-phenyl-2-buten-1-one (10) under atmospheric oxygen affords aromatic N2-substituted 2-pyrimidinamines 9b and c.The dihydropyrimidines 8b and c, probable intermediates of the reactions, could not be isolated.In contrast, heating of arylguanidines 2d,e with 7 leads to stable dihydropyrimidinamines 8d and e, which can be isolated as bases.Addition of methanol to 8d yields 6-methoxy-2-pyrimidinamine 11d, boiling of 8d in DMF affords 9d.Under nitrogen, guanidine adds to 7 to yield aminopyrimidinol 13a, which is transformed by heating in benzene into pyrimidine 9a.The low stability of 8a-c is attributed to their strong basicity, the greater stability of 8d and e to their lower basicity.The structural formulae of 8d, e and 9b-d and their salts respectively were established partly (8e) by nmr and partly (9b-d) by comparison of the corresponding picrates with authentic samples .

Dimroth-Type Ring Transformation of 1,4,6-Trisubstituted-2(1H)-Pyrimidinethiones with Ammonia and Primary Alkyl Amines

1,4,6-Trisubstituted-2(1H)-pyrimidinethiones (Ia-k) underwent Dimroth-type ring transformation with ammonia and prymary alkyl amines in the presence of silver perchlorate to afford 2-(N-substituted)aminopyrimidines (IIa, c, d, f, j, k) and pyrimidinium perchlorates (IIIa-c, e-j), respectively.Furthermore, pyrimidinium perchlorates (III) were converted into 2(1H)-pyrimidinones (IV) in high yields by hydrolysis with concentrated hydrochloric acid.Keywords --- Dimroth-type ring transformation reaction; ammonia; primary alkyl amines; 2-(N-substituted)aminopyrimidines; silver perchlorate; 2-(N-substituted)aminopyrimidinium perchlorates; hydrolysis; concentrated hydrochloric acid