5- Phenyl-2- 2- pyrimidine

Other examples of CN/CC replacement are observed in reactions of l-phenyl-pyrimidin-2(l//)-one with active methylene compounds, such as diethyl malonate and benzoylacetate, giving in good yield 2-oxo-l,2-dihydro-3-pyridinecarboxylate and 3-benzoylpyridin-2(l H)-one, respectively (84CPB2942, 87H2223) (Scheme 8). In a similar way 4,6-dimethyl-1-phenylpyrimidin-2( 1 //)-one, 4,6-dimethyl-1 -phenylpyrimidine-2( 1 //)-thione and 4,6-dimethyl-1 -phenyl-2-phenylimino-1,2-dihydropyrimidine yield with malonitrile 2-amino-4,6-dimethyl-3-pyridinecarbonitrile. In a similar way 2,3-diarylpyrimidin-4(3//)-thiones give with malonitrile CN/CC replacement (84H763) (Scheme 8). The reaction takes a similar course as described in Scheme 7. 

Substituierte 2-Phenyl-pyrimidine werden in waOrig alkoholischer Acetat-Pufferlosung (pH 4,5) unter Ammoniak-Abspaltung zu 2-Phenyl-pyrrolen reduziert4 ... 

Trichlormethyl-2-phenyl-pyrimidine konnen selektiv mit hoher Ausbeute in die ent-sprechenden 4-Dichlormethyl-2-phenyl-pyrimidine iibergefiihrt werden7 ... 

In this section we will report on the crystal structure analyses of mesogenic 2,5-diphenyl pyrimidines. The crystal structure of 5-phenyl-2-(4 -n-butoxy-phenyl)-pyrimidine (5-PBuPP) and 2-phenyl-5-(4 -n-pentoxyphenyl)-pyrimi-dine (2-PPePP) were determined by Winter et al. [83, 84]. Compound 5-PBuPP forms a monotropic nematic phase, whereas compound 2-PPePP exhibits a smectic A mesophase within a wide temperature range. The chemical structure of the mesogenic 2,5-diphenyl pyrimidines is shown in Fig. 13. 

Pyridine-, Phenyl-, Pyrimidine- and Pyrazole-based CB] Receptor Antagonists 295... 

PYRIDINE-, PHENYL-, PYRIMIDINE- AND PYRAZOLE-BASED CBi RECEPTOR ANTAGONISTS... 

The final conditions were scaled up with no problems chalcone 8a and guanidine (liberated from its hydrochloride with sodium ethoxide) were heated in dimethyl acetamide while bubbling air through the mixture to form pyrimidine 9a. After complete conversion (16 h), the product was cleaved from the support (20% trifluoroacetic acid in DCM). Pure 4-(2-amino-6-phenyl-pyrimidin-4-yl)bcnzamidc 1 was obtained as its trifluoroacetate salt upon evaporation of the filtrate and recrystallisation of the residue from ethanol/water in 56% overall yield based on the solid phase attached 4-carboxybenzaldehyde 6a. 

Comparison of this reactivity order with that found in the amination of 2-X-4-phenyl pyrimidines (SCH3 Br = Cl > F > SO2CH3 I > (013)3 > CN see Table 11.5 in Section ll,C,l,d) shows that these reactivity orders differ considerably. The fluoro substituent, especially, which has in the pyrimidine series about the same reactivity order as the chloro or bromo atom, shows in the 1,2,4-triazine series a low ANRORC activity. Comparison of both series of reactivities is, however, a delicate matter, mainly because the yields obtained for the amino compounds in the 1,2,4-triazine series are much lower than those obtained in the pyrimidine series, because of the occurrence of many side reactions, such as ring contraction, dehalogenation, ring transformations, and degenerate ring transformations... 

Die Reaktion von 4-Chlor-5-methyl-2-phenyl-pyrimidin zu 4-Ethinyl-2-phenyl-imidazol wurde bereits im Bd. V/2a, S. 237, beschrieben. Analog lagert sich 5-Amino-4-chlor-2-phenyl-pyrimi-din ebenfalls in fliissigem Ammoniak zu 4-Cyan-2-phenyl-imidazol (35%) um430. 

HjC n -oh H.C.V CHj KNO, h2so4 0-5 1 4,6-Dime thyl-2-hydroxy-5-(4-nltro-phenyl)-pyrimidin 24 286 (Metha- nol) 2... 

H5CS-V ch3 kno3 h2so4 5-10 1 2- Amino-4,6-di-methyl-5-(3-nttro-phenyl)-pyrimidin 42 205 (60 % ige Ethanol) 3... 

JM, NH2 rJU3T KNOj h3so4 35-40 0,05 2-Amino-5-(4- nilro-phenyl- pyrimidin 80 262 3... 

The ANRORC mechanism is also supported by the isolation of a small amount of the open-chain 3-amino-l-phenylallylidene cyanamide (36) (Scheme 2) from the products of the reaction of 2-bromo-4-phenyl-pyrimidine as formed from an adduct structurally related to 35a.100... 

AQ91 CioHbN2 L-phenyl pyrimidine t6n cnj DR DMF PY Bu4N 1 - rm DME Ag/AgCl 12A0 t=0.l6... 

Our group also reported on mixtures of a nematic 2-phenyl-pyrimidine derivative (Felix-2900-03) containing either hexadecylamine-capped CdSe (ranging in size from 2.5 to 5.2 nm) or thioglycolic acid-capped CdTe quantum dots (3.2-4.0 nm in... 

When treated with phosphoryl chloride at room temperature, 4-phenyl-pyrimidine 1,3-dioxide (37) was chlorinated with the loss of one or two oxide functions. The reaction products were a function of temperature (see Scheme 37), and when there was a methyl group in the 5-position the ratio 2-chloro 3- 2-chloro 1-oxide became 3.5 1. If all of the positions a and y to the N-oxide functions were blocked, the usual Meisenheimer process did not occur instead lateral chlorination of the adjacent methyl groups was observed (81CHE383 83CPB4533). No 2- and 4-chloropyrimi-dines were formed on similar treatment of 2- and 6-methylpyrimidine 1-oxides deoxygenation and lateral chlorination only were noted [83H(20)991]. 

Of course, not all methods of cocrystal production require the use of auxiliary solvents. Thermal microscopy was used to determine if a particular carboxylic acid could cocrystallize with 2-[4-(4-chloro-2-fluorophe-noxy)phenyl]pyrimidine-4-carboxamide, with positive interactions being detected as crystalline material being produced at the binary interface [35]. Once identified, authentic cocrystal systems were prepared on a larger scale using solution-phase methods. In a similar study, hot-state microscopy was used to screen the possible interactions of nicotinamide with seven compounds of pharmaceutical interest that contained carboxylic acid groups [36]. A screening method for cocrystal formation based on differential scanning calorimetry has also been described, and used to demonstrate cocrystal formation in 16 out of 20 tested binary systems [37],... 

Fifteen cocrystals of N-[4-( 6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl oxy)-l,3-ben2 othiazol-2-yl]-acetainide... 

C12H10CIN3 4-chloro-6-ethyleneimino-2-phenyl pyrimidine 63019-51-2 422.95 36.533 1,2 23618 C12H11N 1,2-dihydro-5-acenaphthylenamine 4657-93-6 560.13 49.690 2... 

Bromination of 5-allyl-6-methyl-2-methylthio(phenyl)pyrimidine-4-thiols (144) in chloroform afforded 6-bromomethyl-4-methyl-2-melhylthio(phenyl)-5,6-di-hydrothieno[2,3-<7]pyrimidines 145. The latter were transformed into 4,6-dimethyl-2-methylthio(phenyl)thieno[2,3-<7]pyrimidines 146 by refluxing with ethanolic sodium ethoxide (1999KZA60). 

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