4- Methyl-6-chloropyrimidine

Chloropyrimidine is aminated with alcoholic ammonia at 130° while 4-chloro-2-methyl- and 4-chloro-6-methyl-pyrimidine yield the corresponding 4-amino derivatives at 100°. 4-Aminopyrimi-dine is not prepared from the chloro analog because of facile self-quatemization (see Section III, B, 2 for comments on factors involved) of the latter. 

Amino group of 7-aminomethyl-2-substituted perhydropyrido[l,2-u]pyr-azines were reacted with 2-bromopyridine and 2-chloropyrimidines to give 7-(hetarylamino)methyl derivatives in the presence of Na2C03 in DMF at 100-120°C for 18h in 13-51% yields (00MIP15). An aminomethyl group of... 

Brompheniramine maleate Chlorpheniramine meleate Methyl phenidate HCI Tranzodone HCI 2-Chloropyrimidine Piribedil... 

The influence of the nature of the substituent at position 4. In order to determine the influence of substituents at position 4 on the Sn(ANRORC) process in the aminodehalogenation, the amide-induced amination was studied with 6-chloropyrimidines containing different substituents at position 4, i.e., the 4-Ubutyl-, 4-methoxy-, 4-piperidino-, 4-anilino-, and 4-methyl-groups (79RTC5). The results are summarized in Table ILl. 

Van der Plas and coworkers have devised a synthesis of 2-substituted 4-methyl-l,3,5-triazines (182) by treatment of 2-substituted 4-chloropyrimidines with potassium amide in... 

A mixture of (-)-(R)-N-[(3,4-dihydro-2H-l-benzopyran-2-yl)methyl]-l,3-propanediamine, 2-chloropyrimidine, sodium carbonate and ethanol was stirred for 4 h at reflux temperature. The reaction mixture was evaporated. The residue was purified by column chromatography (silica gel CHCI3/CH3OH 90 10). The eluent of the desired fraction was evaporated and the residue was converted into the hydrochloride salt in 2-propanol. The salt was filtered off and dried in vacuum, yielding (-)-(R)-N-[(3,4-dihydro-2H-l-benzopyran-2-yl)methyl]-N -(2-pyrimidinyl)-l,3-propanediamine dihydrochloride hemihydrate. 

Furo[2,3-r/]pyrimidines can also be obtained from other 6-substituted-pyrimidines. For example, the 6-chloropyrimidine (219) is converted to the 6-propargyloxy compound (220) which cyclizes to the derivative (221) upon heating <84H(22)2217>. The formation of a 6-methyl isomer is accounted for by a Claisen rearrangement of the 6-allyloxy group (Scheme 16). 

Syntheses from precursors of types (405) and (406) are rare, and of type (407) are unknown. One example of the first of these is the oxidative cyclization of pyrimidine (408) to the glycosyl pyrimidotriazine (409) (Equation (68)) <82MI 720-01). An interesting example of the second type is the cyclization of the 6-chloropyrimidine (411). In the presence of air this affords 2-methyl-fervenulone (412) by straightforward intramolecular nucleophilic substitution of the chlorine atom. Pyrolytic cyclization of compound (411), however, affords the isomeric 1-methyl product (413), possibly via a diaziridine intermediate (Scheme 33) <75JOC232i>. 

The anionic form of 5-chloropyrimidin-2( 1 H)-one, particularly under phase-transfer conditions, was selectively methylated and benzylated at... 

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