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Chemical Structure| 7749-47-5 Chemical Structure| 7749-47-5

Structure of 7749-47-5

Chemical Structure| 7749-47-5

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Product Details of [ 7749-47-5 ]

CAS No. :7749-47-5
Formula : C6H9N3O
M.W : 139.15
SMILES Code : C1=C(N=C(N)N=C1C)OC
MDL No. :MFCD00059768
InChI Key :SNWZXTZIZWBIDQ-UHFFFAOYSA-N
Pubchem ID :587236

Safety of [ 7749-47-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 7749-47-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 7749-47-5 ]

[ 7749-47-5 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 7749-47-5 ]
  • [ 121-60-8 ]
  • [ 36082-36-7 ]
YieldReaction ConditionsOperation in experiment
20% With pyridine; at 0 - 60℃; for 17.0h; Step 1: Synthesis of N-{4-[(4-methoxy-6-methylpyrimidin-2-yl)sulfamoyl] phenyl}acetamide 19.1 [00351] 4-(Acetylamino)benzenesulfonyl chloride (2.00 g, 8.56 mmol) was added at 0C to a stirred solution of <strong>[7749-47-5]4-methoxy-6-methylpyrimidin-2-amine</strong> (1.19 g, 8.56 mmol) in pyridine (dry, 20ml). The reaction mixture was allowed to reach rt and stirred for 15h then heated to 60C for 2h. The solvent was removed in vacuo by azeotroping with toluene (2 x 25ml), followed by n- heptane (2 x 25ml) to afford a brown oil which was purified by flash column chromatography (MeOH/DCM 0/100 to 5/95) to obtain 0.60g (20%) of N-{4-[(4-methoxy-6-methylpyrimidin-2- yl)sulfamoyl]phenyl}acetamide 19.1 a colourless solid.
With pyridine; at 60℃; for 12.0h; Step 1 - N-[4-[(4-methoxy-6-methyl-pyrimidin-2-yl)sulfamoyl]phenyl]acetamide (0431) [00295] To a suspension of 4-methoxy-6-methyl-pyrimidin-2-amine (4.00 g, 28.8 mmol) in pyridine (40 mL) was added 4-acetamidobenzenesulfonyl chloride (7.05 g, 30.2 mmol, CAS121-60-8). The reaction mixture was stirred at 60 C for 12 hr. On completion, the reaction mixture was concentrated and the residue was diluted with water, the solid was filtered, washed with dichloromethane (30 mL), and dried under vacuum to give the title compound. LCMS: (ES- ) m/z (M-H)- = 335.1, tR = 1.011.
  • 3
  • [ 7749-47-5 ]
  • [ 22536-64-7 ]
YieldReaction ConditionsOperation in experiment
8% With hydrogenchloride; sodium nitrite; In water; at 0 - 20℃; for 1.5h; To a solution 2-amino-4-methoxy-6-methylpyrimidine (5 g, 35.97 mmol) in aqueous concentrated HCl (50 ml) was added NaNO2 (2.97 g, 43.16 mmol) in water(5 ml) slowly drop by drop over a period 30 min at 0oC and then the reaction mixture was stirred at room temperature for 1 hour. Then, the reaction mixture was quenched with 10 N sodium hydroxide solution then insoluble material was, filtered and filtrate was partitioned between brine and AcOEt and the aqueous layer was extracted with AcOEt. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give a brown oil. The crude compound which upon purification by flash chromatography using (silica-gel: 100-200 mesh, AcOEt -petroleum ether; 10:90→ 15:85) gave 600 mg (yield 8%) of a white solid corresponding to 2-chloro-4-methoxy-6- methylpyrimidine.
With sodium nitrite; In hydrogenchloride; water; EXAMPLE 6 2-Chloro-4-methyl-6-methoxypyrimidine A solution of 25.4 g of 2-amino-4-methyl-6-methoxypyrimidine in 150 ml concentrated hydrochloric acid was cooled to ca. 0 C. and treated with a solution of 25.3 g of sodium nitrite in 50 ml water, added over a period of 30-40 minutes. The thick orange reaction mixture was stirred at room temperature for 4-5 hours and then adjusted to pH 10 by addition of 12.5N sodium hydroxide solution. The precipitate was filtered and extracted thoroughly with approximately 600 ml of hot ether. The organic layer was dried over magnesium sulfate and concentrated in vacuo to give 7.2 g of 2-chloro-4-methyl-6-methoxypyrimidine as a white, crystalline solid, m.p. 36-38 C. NMR(CDCl3): δ 6.5 (1H, s, heterocyclic H); 4.0 (3H, s, --OCH3); 2.4 (3H, s, --CH3).
  • 4
  • [ 7749-47-5 ]
  • 3-Isocyanatosulfonyl-1-methyl-1H-indole-2-carboxylic acid methyl ester [ No CAS ]
  • 3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-1-methyl-1H-indole-2-carboxylic acid, methyl ester [ No CAS ]
  • 5
  • [ 7749-47-5 ]
  • [ 98-60-2 ]
  • [ 353302-84-8 ]
  • 6
  • [ 7749-47-5 ]
  • [ 98-59-9 ]
  • [ 330946-56-0 ]
  • 7
  • [ 7749-47-5 ]
  • [ 98-11-3 ]
  • [ 312597-84-5 ]
  • 8
  • [ 7749-47-5 ]
  • [ 2905-23-9 ]
  • [ 130240-03-8 ]
  • 9
  • [ 7749-47-5 ]
  • [ 140160-21-0 ]
  • 1-(4-methoxy-6-methyl-pyrimidin-2-yl)-3-[5-(4-nitro-phenyl)-furan-2-carbonyl]-thiourea [ No CAS ]
  • 10
  • [ 7749-47-5 ]
  • [ 304437-60-3 ]
  • 1-[5-(2-chloro-phenyl)-furan-2-carbonyl]-3-(4-methoxy-6-methyl-pyrimidin-2-yl)-thiourea [ No CAS ]
  • 11
  • [ 936020-75-6 ]
  • [ 7749-47-5 ]
  • C12H15N5O2S2 [ No CAS ]
  • 12
  • [ 7749-47-5 ]
  • 5-Methoxy-2,7-dimethyl-imidazo[1,2-a]pyrimidine-3-carboxylic acid [ No CAS ]
  • 13
  • [ 7749-47-5 ]
  • 5-methoxy-7-methylimidazo<1,2-a>pyrimidine-2-carboxylic acid [ No CAS ]
  • 14
  • [ 7749-47-5 ]
  • 5-methoxy-7-methylimidazo<1,2-a>pyrimidine-2-carboxamide [ No CAS ]
  • 16
  • [ 7749-47-5 ]
  • ethyl (N-methylsulfonyl-N-methylamino)sulfonylcarbamate [ No CAS ]
  • 1-[(N-methylsulfonyl-N-methylamino)-sulfonyl]-3-(4-methoxy-6-methyl-2-pyrimidinyl)-urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
96.4% In chlorobenzene; EXAMPLE 2 1-[(N-Methylsulfonyl-N-methylamino)sulfonyl]-3-(4-methoxy-6-methyl-2-pyrimidyl)urea 52.0 g of ethyl (N-methylsulfonyl-N-methylamino)sulfonylcarbamate are dissolved in 500 ml of chlorobenzene, 27.8 g of 2-amino-4-methoxy-6-methylpyrimidine are added at room temperature, and the mixture is heated at 50 C. for 5 hours. After cooling to 0 C., the precipitate is filtered off. After washing with 100 ml of chlorobenzene, 68.8 g of the desired product of a purity of 98.9% are obtained; this corresponds to a yield of 96.4% of theory. The melting point of the product is 118-120 C.
  • 17
  • [ 7749-47-5 ]
  • [ 3611-92-5 ]
  • 1-[(N-methylsulfonyl-N-methylamino)-sulfonyl]-3-(4-methoxy-6-methyl-2-pyrimidinyl)-urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; EXAMPLE 19 1-[(N-methylsulfonyl-N-methylamino)-sulfonyl]-3-(4-methoxy-6-methyl-2-pyrimidinyl)-urea 13.9 g (0.1 mol) of 2-amino-4-methoxy-6-methylpyrimidine are suspended in 150 ml of methylene dichloride, and 21.4 g (0.1 mol) of N-methylsulfonyl isocyanate in 50 ml of methylene dichloride are added at 0 C. in the course of one hour. Stirring is continued for 15 hours at room temperature and the product is then precipitated with n-hexane. 20.4 g (58% of theory) of 1-[(N-methylsulfonyl-N-methylamino)-sulfonyl]-3-(4-methoxy-6-methyl-2-pyrimidinyl)-urea of melting point 118-120 C. are obtained.
  • 18
  • [ 7749-47-5 ]
  • [ 114332-63-7 ]
  • [ 60-29-7 ]
  • [ 4223-09-0 ]
  • [ 102410-14-0 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; EXAMPLE 8 N-[(4-Methyl-6-methoxypyrimidin-2-yl)aminocarbonyl]-2-[5-(methylthio)-1,3,4-oxadiazol-2-yl]benzenemethanesulfonamide To a suspension of 0.33 g of 2-amino-4-methyl-6-methoxypyrimidine in 10 ml of acetonitrile was added 1 g of crude sulfonyl isocyanate prepared in Example 7. The suspension was stirred at room temperature overnight, then filtered. The residue was washed with 25 ml of ethyl ether and suction dried to give 0.7 g of the subject compound; m.p. 194-196 C. NMR(CDCl3, DMSO): ppm δ2.3 (s, 3H, CH3) 2.8 (s, 3H, SCH3); 3.8 (s, 3H, OCH3); 5.6 (s, 2H, CH2); 6.3 (s, 1H, pyrimidin); 7.4-7.9 (m, 4H, arom.). IR (nujol): 1710 cm-1 (C=O).
  • 19
  • ammonium thiocyanate [ No CAS ]
  • [ 7749-47-5 ]
  • [ 98-88-4 ]
  • [ 93744-71-9 ]
  • N-[[(4-methoxy-6-methylpyrimidin-2-yl)aminothiocarbonyl]amino]benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; EXAMPLE 3 N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminothioxomethyl]benzamide To a hot solution of 14 g of ammonium thiocyanate in 300 ml of acetonitrile was added 24 ml of benzoyl chloride. The mixture was heated on the steam bath for 30 minutes and filtered. The filtrate was heated with 21 g of 4-methoxy-6-methylpyrimidine-2-amine for 30 minutes and cooled. The product was collected by filtration and washed with a little acetonitrile to provide 28 g of N-[[(4-methoxy-6-methylpyrimidin-2-yl)aminothiocarbonyl]amino]benzamide, m.p. 193-195. IR (Nujol) 3290, 1720 cm-1.
  • 20
  • aluminum (III) chloride [ No CAS ]
  • [ 7749-47-5 ]
  • [ 1189-71-5 ]
  • [ 37493-34-8 ]
  • 3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-1-methyl-1H-indole-2-carboxylic acid, methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
In CH3 NO2; nitromethane; dichloromethane; acetone; EXAMPLE 2 Preparation of Methyl 3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-1-methyl-1H-indole-2-carboxylate To a stirred suspension of 2.92 g (0.021 mole) of 2-amino-4-methoxy-6-methylpyrimidine in 75 ml dry CH3 NO2 at -10 was addded dropwise under nitrogen via syringe 2.0 ml (0.023 mole) of chlorosulfonyl isocyanate at such a rate as to maintain the temperature below 0. The resulting clear solution was stirred 0.5 hour at -5 to -10 and then contacted dropwise with a solution of 3.97 g (0.021 mole) of methyl 1-methyl-1H-indole-2-carboxylate dissolved in 25 ml of dry nitromethane. Upon completion of the addition, 2.95 g (0.022 mole) of aluminum (III) chloride was added in one portion. The reaction mixture was stirred at reflux for 3 hours, then cooled to room temperature and poured into 300 ml H2 O. Dichloromethane was added and the layers were separated. The aqueous solution was extracted with two additional portions of CH2 Cl2 and the combined organic solutions washed with H2 O, dried over MgSO4 and evaporated in vacuo. Chromatography on silica gel with 5% acetone in CH2 Cl2 afforded 1.63 g of the desired product as a white solid, m.p. 200-203 (d). The infrared spectrum of the product included absorptions at 3190 (NH), 1715 (C=O), 1703 (C=O), 1340 and 1150 (SO2) cm-1, 'H NMR (CDCl3 /DMSO-d6) δ2.45 (s, 3H, pyrimidine CH3), 3.95 (s, 3H, OCH3), 4.0 (s, 6H, OCH3 and N--CH3), 6.37 (s, 1H, pyrimidine CH), 7.23-7.56 (m, 3H, indole CH), 8.18-8.47 (m, 1H, indole CH), 9.50 (s, 1H, NH), 13.08 (br s, 1H, NH). Mass spectral analysis showed m/e 139, STR31
  • 21
  • [ 7749-47-5 ]
  • [ 106-54-7 ]
  • 2-[(4-chlorophenylthio)methylamino]-4-methoxy-6-methylpyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With formaldehyd; acetic acid; In methanol; toluene; EXAMPLE 1 Preparation of 2-[(4-chlorophenylthio)methylamino]-4-methoxy-6-methylpyrimidine (intermediate) STR25 A mixture of 13.99 g of 2-amino-4-methoxy-6-methylpyrimidine (0.1 mole), 14.8 g of 4-chlorothiophenol (0.1 mole), 9.4 g of aqueous 35% formaldehyde (0.11 mole) and 1 g of acetic acid are heated under reflux for 1 hour in 100 ml of methanol. The resultant solution is clarified by filtration, diluted with 150 ml of toluene and then the solvent is removed in a rotary evaporator. The residue crystallises after standing for some time. The melting point is 78-82 after recrystallisation from hexane. The yield is 24 g (81% of theory).
  • 22
  • [ 288-88-0 ]
  • [ 7749-47-5 ]
  • 4-methoxy-6-methyl-2-(1,2,4-triazol-1-ylmethylamino)pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With formaldehyd; acetic acid; In methanol; EXAMPLE 5 Preparation of 4-methoxy-6-methyl-2-(1,2,4-triazol-1-ylmethylamino)pyrimidine STR32 With stirring, a mixture of 13.9 g (0.1 mole) of 2-amino-4-methoxy-6-methylpyrimidine, 7 g (0.1 mole) of 1,2,4,-triazole, 9.4 g (0.11 mole) of aqueous 35% formaldehyde and 1 g of acetic acid in 100 ml of methanol is refluxed for 11/2 hours. First a clear solution forms, from which the reaction product precipitates in crystalline form after a time. After the reaction mixture has cooled, the crystalline title compound is filtered with suction and dried. Yield: 14 g. Melting point: 191-193 C.
  • 23
  • [ 7749-47-5 ]
  • aqueous NaCl [ No CAS ]
  • [ 616-38-6 ]
  • [ 83060-43-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In tetrahydrofuran; EXAMPLE 6 Methyl (4-methoxy-6-methylpyrimidin-2-yl)carbamate 2-Amino-4-methoxy-6-methylpyrimidine (50 g) was added portion wise to 50% sodium hydride (42.8 g) in 1 L dry THF. After stirring for 1/2 hour, dimethyl carbonate (58.5 g) was added dropwise with cooling. The mixture was stirred under nitrogen for ~16 hours at ambient temperature. Concentrated HCl (80 ml) was added slowly and using external cooling a pot temperature of ~25 C. was maintained. Saturated aqueous NaCl (80 ml) was then added. The solvents were decanted from the precipitated solids and dried over Na2 SO4. Filtering and evaporating the solvents afforded the crude material which was recrystallized from hexane. 54 g m.p. 89-92.5 C. The infrared spectrum showed characteristic absorption bonds at 3400 and 1760 cm-1.
  • 24
  • [ 75-44-5 ]
  • [ 7749-47-5 ]
  • 1,4-diaza[2.2.2]bicyclooctane [ No CAS ]
  • [ 41570-86-9 ]
  • [ 111-36-4 ]
  • N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-acetoxy-3,5-dichlorobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% In dichloromethane; c. N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-acetoxy-3,5-dichlorobenzenesulfonamide A mixture of 6.0 gm (0.02 mole) 2-acetoxy-3,5-dichlorobenzenesulfonamide, 0.1 gm 1,4-diaza[2.2.2]bicyclooctane (DABCO), 2.8 ml (0.025 mole) n-butyl isocyanate and 50 ml dry xylenes was heated to reflux and maintained at that temperature for 1 hour. Phosgene (0.03 mole, 1.3 ml) was then added dropwise, so as to maintain the reaction temperature >130. The reaction mixture was boiled under reflux for 3 hours after addition of phosgene, then cooled and filtered. The solvent was removed in vacuo and the residue was dissolved in 20 ml of methylene chloride and added directly to a stirred solution of 2-amino-4-methoxy-6-methylpyrimidine in 10 ml methylene chloride. The reaction was protected from atmospheric moisture and stirred overnight. Filtration of the solution removed excess starting material and the solution was evaporated to a residue. The residue was washed with 1-butyl chloride and filtered, giving 1.4 g (0.003 mole, 22% yield) of the sulfonylurea product. The nuclear magnetic resonance of the product shows peaks as follows: (singlet, 2.0δ, 3H, singlet, 2.2δ, 3H; singlet, 3.9δ, 3H; singlet, 6.1δ, 1H; 7.5-8.2δ, multiplet, 2H; br singlet, 8.6δ, 1H), consistent with the desired product.
  • 25
  • [ 7749-47-5 ]
  • N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(methylsulfonyl)-3-thiophenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; EXAMPLE 6 N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methylsulfonyl-3-thiophenesulfonamide The crude 2-methylsulfonyl-3-thiophenesulfonyl isocyanate described above was dissolved in 100 ml of methylene chloride and 10 ml of this solution (0.3 g of crude isocyanate) was added to 200 mg of 4-methoxy-6-methyl-2-pyrimidinamine in methylene chloride containing a few crystals of DABCO. After stirring 3 days at room temperature, the precipitate was filtered and washed with ether to afford 250 mg of product, m.p. 204.5-206 d. The IR spectrum showed a carbonyl absorption at 1680 cm-1 indicative of a sulfonylurea.
  • 26
  • [ 7749-47-5 ]
  • [ 77888-53-0 ]
  • N'-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-N,N-diethyl-1,2-benzenedisulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; EXAMPLE 5 N,N-Diethyl-N'-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide A mixture of 0.8 g of 2-amino-4-methoxy-6-methylpyrimidine, 2.8 g of the crude sulfonyl isocyanate from Example 4 and a few crystals of DABCO in 25 ml of acetonitrile was stirred at room temperature for 16 hours. A small amount of unreacted aminopyrimidine was filtered off and the filtrate concentrated in-vacuo to give a hard glass. Crystallization from methanol gave 0.9 g of N,N-diethyl-N'[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide as a white solid, m.p. 170-2. Anal. Calcd. for C17 H23 N5 O6 S2: C, 44.62; H, 5.07; N, 15.31. Found: C, 44.5, 44.4; H, 5.09, 5.09; N, 15.4, 15.5. NMR(DMSO-d6)δ: 0.9-1.2 [t,6.0H, (CH3 CH2)2 N-]; 2.3 (S, 2.8H, Het--CH3); 3.1-3.5 [qt, 4.3H, (CH3 CH2)2 N-]; 3.9 (S, 3.0H, Het--OCH3); 6.5 (S, 0.9H, Het--H); 7.7-8.5 (m, 4.3H, 4 aromatics); 10.6 (S, 1.0H, NH); 13.4 (S, 0.8H, NH).
  • 27
  • [ 7749-47-5 ]
  • [ 79163-69-2 ]
  • 8-nitro-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1-naphthalenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; EXAMPLE 5 8-nitro-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1-naphthalenesulfonamide To 0.55 g (0.004 mol) of 2-amino-4-methoxy-6-methylpyrimidine dissolved in 5 ml of dry methylene chloride in a magnetically stirred 50 ml round bottom flask equipped with reflux condenser protected from moisture was added 4 ml of a methylene chloride solution of 1.0 g (0.004 mol) of 8-nitro-1-naphthalenesulfonylisocyanate. The reaction mixture was stirred with heating under reflux for ~16 hours. The cooled reaction mixture was concentrated in vacuo. The crude product was isolated by elutriation with chlorobutane in the usual manner to yield an off white solid, m.p. 145-154.
  • 28
  • [ 7749-47-5 ]
  • 2-hydroxybenzenesulfonylisocyanate, methanesulfonate [ No CAS ]
  • 2-hydroxy-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide, methanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; EXAMPLE 3 2-Hydroxy-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide, methanesulfonate To a suspension of 0.6 g 2-amino-4-methoxy-6-methylpyrimidine in 10 ml dry methylene chloride is added 1.1 g 2-hydroxybenzenesulfonylisocyanate, methanesulfonate. The reaction exotherms mildly and is then stirred for 1/2 hour. The solvent is evaporated under reduced pressure. The resultant mixture is triturated with diethylether and filtered to give 0.95 g white solid m.p. 189-190 C. The infrared spectrum shows absorption bands at 1700, 1615, 1560, 1370 cm-1. Calc. for C-40.4, H-3.87, N-13.4. Found C-40.2, H-3.77, N-13.6.
  • 29
  • [ 7749-47-5 ]
  • [ 90139-98-3 ]
  • N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium hydroxide; In water; acetonitrile; EXAMPLE 4 N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamide To a stirred suspension of 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine in 20 ml of dry acetonitrile at room temperature is added 2.2 g of 2-pyridinesulfonylisocyanate. The mixture is stirred for several hours and filtered. Evaporation of the filtrate yields a solid residue which is stirred in approximately 30 ml of water while adjusting the pH of this mixture to 11 by the addition of 10% NaOH. This solution is filtered, the filtrate pH adjusted to pH 7 by adding 10% hydrochloric acid and the resulting neutral solution again filtered. The desired product is then precipitated from this filtrate by adjusting the pH to 2, collecting in a sintered funnel and drying in a vacuum oven at room temperature.
  • 30
  • [ 7749-47-5 ]
  • [ 74222-95-0 ]
  • [ 74222-99-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In dichloromethane; water; EXAMPLE 5 N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide To a stirred suspension of 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine in 30 ml of anhydrous methylene chloride was added at ambient temperature 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate. After stirring for 16 hours, the foregoing mixture was filtered to remove unreacted amine, and the filtrate evaporated at temperatures up to 40 and reduced pressure. The resultant residue was stirred in 25 ml of water, the pH adjusted to 10 by the addition of 50% sodium hydroxide and the solution filtered. Acidification of the filtrate to pH 3 with hydrochloric acid caused precipitation of the desired product which was removed by filtration and dried to yield 0.8 g of product melting at 173-179. It showed infrared absorption peaks at 1720, 1680, 1630 and 1550 cm-1, consistent for N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide.
With sodium hydroxide; In dichloromethane; water; EXAMPLE 5 N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide To a stirred suspension of 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine in 30 ml of anhydrous methylene chloride was added at ambient temperature 2.4 g of 2-methoxycarbonylbenzenesulfonyl isocyanate. After stirring for 16 hours, the foregoing mixture was filtered to remove unreacted amine, and the filtrate evaporated at temperatures up to 40 and reduced pressure. The resultant residue was stirred in 25 ml of water, the pH adjusted to 10 by the addition of 50% sodium hydroxide and the solution filtered. Acidification of the filtrate to pH 3 with hydrochloric acid caused precipitation of the desired product which was removed by filtration and dried to yield 0.8 g of product melting at 173-179. It showed infrared absorption peaks at 1720, 1680, 1630 and 1550 cm-1, consistent for N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide.
  • 31
  • [ 7749-47-5 ]
  • [ 81885-36-1 ]
  • [ 81885-41-8 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; EXAMPLE 8 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzothiophene-3-sulfonamide To 25 ml of anhydrous acetonitrile containing 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine was added 2.4 g of benzothiophene-3-sulfonyl isocyanate with stirring. The mixture was heated to boiling, allowed to cool to room temperature and then stirred overnight. The resultant precipitate was filtered off and washed with ether to yield 2 g of the desired product, m.p. 180-181 C. It showed absorption by NMR (60 MC) at 2.24 δ (6-CH3 group), 3.8 δ (4-OCH3), 6.2 δ (5-H on pyrimidine), 7-8 δ (aryl H's on benzo) and 8.3 δ (H on thiophene portion). Anal. Calcd. for C15 H14 N4 O4 S2: C, 47.61; H, 3.77; N, 14.81. Found: C, 47.59; H, 3.88; N, 14.83.
  • 32
  • [ 7749-47-5 ]
  • [ 76833-95-9 ]
  • [ 76833-96-0 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; EXAMPLE 12 N-[(4-Methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl]-4-nitrothiophene-2-sulfonamide To 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine in 25 ml of anhydrous acetonitrile was added 2.4 g of 4-nitrothiophene-2-sulfonyl isocyanate with stirring at ambient temperature. After stirring for sixteen hours, the mixture was filtered and the precipitate washed with 1-chlorobutane. It melted at 155 with decomposition and showed an infrared absorption spectrum with peaks at 1700, 1620 and 1570 cm-1 consistent for the desired structure.
  • 33
  • [ 7749-47-5 ]
  • 2-(1-cyclopentenyl)benzenesulfonyl isocyanate [ No CAS ]
  • 2-(1-cyclopentenyl)-N-[(4-methoxy-6-methylpyrimidin-2-yl)-aminocarbonyl]benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,4-diaza-bicyclo[2.2.2]octane; In dichloromethane; EXAMPLE 10 2-(1-Cyclopentenyl)-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide A mixture of 2-amino-4-methoxy-6-methylpyrimidine (0.45 g, 3.2 mmol), methylene chloride and DABCO (ca. 10 mg) was contacted with 2-(1-cyclopentenyl)benzenesulfonyl isocyanate in methylene chloride solution at ambient temperature. After approximately 20 minutes the product crystallized from the reaction mixture and was collected by filtration and rinsed with ether. In this manner, 0.35 g of product was obtained, m.p. 235-236. The infrared spectrum exhibited a carbonyl absorption at 1710 cm-1 indicating the title compound.
  • 34
  • [ 7749-47-5 ]
  • [ 616-38-6 ]
  • [ 83060-43-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In tetrahydrofuran; EXAMPLE 6 Methyl (4-methoxy-6-methylpyrimidin-2-yl)carbamate To a suspension of 50 g of 2-amino-4-methoxy-6-methylpyrimidine in 1000 ml of tetrahydrofuran was added portionwise, under a nitrogen atmosphere, 42.8 g of 50% sodium hydride while cooling the reaction flask in an ice-water bath. After stirring one hour at 25 C., 58.5 g of dimethylcarbonate was added dropwise at 5 to 25 C. The suspension was stirred about 16 hours at ambient temperature, then 80 ml of concentrated hydrochloric acid was added dropwise while maintaining a reaction temperature of 20 to 25 C. with external ice-bath cooling. The suspension was stirred 0.5 hour, filtered, and the filtrate was dried over sodium sulfate and then concentrated in vacuo. The residue was recrystallized from hexane to yield 54 g of the title compound, m.p. 89-92.5 C.
  • 35
  • [ 7749-47-5 ]
  • 2,3-dihydro-5-nitro-1H-indenesulfonyl isocyanate [ No CAS ]
  • [ 87473-77-6 ]
  • 2,3-dihydro-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-5-nitro-1H-indene-4-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; EXAMPLE 3 2,3-Dihydro-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-5-nitro-1H-indene-4-sulfonamide To 0.69 g of 2-amino-4-methoxy-6-methylpyrimidine suspended in 5 ml of anhydrous methylene chloride was added with stirring one fifth of the solution of 2,3-dihydro-5-nitro-1H-indenesulfonyl isocyanate prepared in Example 1. After stirring at reflux for 16 hours, the methylene chloride was removed in vacuo on a rotary evaporator and the residue was triturated with 1-chlorobutane and methylene chloride to yield a solid which decomposed at 75-93. This product showed absorption peaks by infrared spectroscopy at 3400 cm-1 (NH), 1670 cm-1 (CO), 1540 cm-1 (NO2) and 1360 cm-1 (SO2). The structure was confirmed by Proton Magnetic Resonance absorption peaks at 7.6 ppm (aromatic CH), 6.4 ppm (pyrimidine CH), 2.8-3.6 ppm (cyclic CH2) and 3.9 ppm (CH3 O).
 

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