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[ CAS No. 38696-20-7 ]

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2D
Chemical Structure| 38696-20-7
Chemical Structure| 38696-20-7
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Product Details of [ 38696-20-7 ]

CAS No. :38696-20-7MDL No. :MFCD09999220
Formula : C10H7BrN2 Boiling Point : 232°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :235.08Pubchem ID :14387745
Synonyms :

Computed Properties of [ 38696-20-7 ]

TPSA : 25.8 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 1

Safety of [ 38696-20-7 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 38696-20-7 ]

  • Upstream synthesis route of [ 38696-20-7 ]
  • Downstream synthetic route of [ 38696-20-7 ]

[ 38696-20-7 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 183438-24-6 ]
  • [ 98-80-6 ]
  • [ 38696-20-7 ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate In 1,4-dioxane; water at 110℃; Microwave irradiation Intermediate 21; <n="54"/>A mixture of 5-bromo-2-iodopyrimidine (1.76 mmol, 0.500 g), phenylboronic acid (1.93 mrnol, 0.235 g), 2M aqueous solution of K2CO3 (4.40 mmo., 2.2 m.), Pd(PPh3J4 (0.18 mmol, 0.203 g) in dioxane (10 ml) was heated at 11O0C overnight in a microwave oven. The solvent was evaporated and the solid residue was extracted between water and ethyl acetate. The organic phase was evaporated and the crude residue was purified by chromatography over SiO2 eluting with hexane/ethyl acetate mixtures affording 0.329 g (yield 65percent) of the expected product.ESI/MS (m/e, percent): 235 [(M+1)\\ 100], 237 [(M+1)+, 97].
59% With tetrakis(triphenylphosphine)palladium (0) In hexane; water; ethyl acetate; toluene Step 1:
Synthesis of 5-bromo-2-phenylpyrimidine
First, 1.97 g of 5-bromo-2-iodopyrimidine, 0.85 g of phenylboronic acid, 7.0 mL of a 2M sodium carbonate aqueous solution, and 18 mL of toluene were put in a 200-mL three-neck flask equipped with a reflux pipe, and the atmosphere in the flask was replaced with nitrogen.
After the mixture was degassed by being stirred under reduced pressure, 0.081 g of tetrakis(triphenylphosphine)palladium(0) (abbreviation: Pd(PPh3)4) was added thereto and the mixture was refluxed for 8 hours.
Here, 0.040 g of Pd(PPh3)4 was added and the mixture was refluxed for 8 hours, and then, 0.040 g of Pd(PPh3)4 was further added and the mixture was further refluxed for 8 hours to cause a reaction.
Water was added to the resulted solution, and an organic layer was extracted with dichloromethane.
The obtained solution of the extract was washed with saturated brine, and magnesium sulfate was added for drying.
The solution obtained by the drying was filtrated.
The solvent of this solution was distilled off, and then the obtained residue was purified by flash column chromatography using hexane and ethyl acetate as a developing solvent in a ratio of 5:1, so that the objective pyrimidine derivative (white powder) was obtained in a yield of 59percent).
A synthetic scheme of Step 1 is shown in (b-1) below.
59% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene for 24.00 h; Inert atmosphere; Reflux First of all, 5-bromo-2-iodopyrimidine 1.97g and phenyl boronic acid 0.85g, 2M sodium carbonate aqueous solution 7.0mL, toluene 18mL, reflux condenser put in a 200mL three-necked flask equipped with a, in the flask was replaced with nitrogen. After degassing with stirring under reduced pressure, tetrakis (triphenylphosphine) palladium (0) (abbreviation: Pd (PPh 3 ) 4 ) 0.081 g and the mixture was refluxed for 8 hours. Here, Pd (PPh 3 ) 4 0.040 g was added, and the mixture was refluxed for 8 hours, more Pd (PPh 3 ) 4 0.040 g was added and reacted by refluxing for 8 hours. Water was added to the reaction solution, and the organic layer was extracted with dichloromethane. The resulting extract was washed with saturated brine, and dried over magnesium sulfate. After the drying, the solution was filtered. After evaporating the solvent of this solution, the resulting residue, hexane: ethyl acetate = 5: 1 was purified by flash column chromatography as a developing solvent, to give a pyrimidine derivative of interest (white powder, yield: 59percent).
50% With sodium carbonate In water; toluene for 42.00 h; Heating / reflux Step 1:
5-Bromo-2-phenyl-pyrimidine
To a degassed solution of phenylboronic acid (8.93 g, 73.22 mmol, 1.0 equiv; commercially available), 5-bromo-2-iodo-pyrimidine (20.86 g, 73.22 mmol, 1.0 equiv; commercially available) and tetrakis(triphenylphosphine) palladium(0) (0.85 g, 0.73 mmol, 0.01 equiv) in toluene (180 mL) was added Na2CO3 (15.52 g, 146.45 mmol, 2.0 equiv), dissolved in water (60 mL), and the reaction mixture heated to reflux.
After 18 h, tetrakis(triphenylphosphine) palladium(0) (0.42 g, 0.37 mmol, 0.005 equiv) was added and the reaction mixture heated for an additional time period of 24 h.
The solvent was removed under reduced pressure and the crude reaction product extracted from a sat. solution of NaCl (200 mL) with ethyl acetate (3*150 mL).
The combined organic phases were dried over Na2SO4, concentrated by evaporation under reduced pressure and the crude material purified by silica column chromatography eluding with heptane/ethyl acetate (9:1) to provide 8.60 g (50percent) of the title compound.
38% With sodium carbonate In water; toluene at 115℃; for 16.00 h; Inert atmosphere A mixture consisting of 5-bromo-2-iodopyrimidine (Bridge Organics, 10.0 g, 35.1 mmol), benzene boronic acid (Alfa Aesar, 4.25 g, 35.1 mmol), tetrakis(triphenylphosphine)palladium (Strem, 0.405 g, 0.351 mmol), toluene (150 mL), and a 2 M aqueous sodium carbonate solution (35 mL) was stirred at 115° C. (degrees Celsius) under a nitrogen atmosphere for 16 hours.
After cooling to room temperature, the mixture was partitioned between chloroform (250 mL) and brine (200 mL).
The phases were separated and the organic phase was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give an orange oil (9.1 g).
The crude product was purified by flash silica column chromatography.
Elution through a 500-g Analogix.(R). flash silica cartridge with 100percent hexanes afforded the title intermediate as a white solid (3.15 g, 38percent yield). Rf 0.69 with 9:1 v/v hexanes-ethyl acetate; 1H-NMR (400 MHz; CDCl3) δ 8.83 (s, 2H), 8.44-8.38 (m, 2H), 7.52-7.46 (m, 3H); MS (APCI+) m/z 236.9 (M+1).
35% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 20 - 80℃; for 2.00 h; Inert atmosphere To a stirred solution of compound 361 (1.4 g) in DMF: H20 (4:1, 20 mL) were added sodium carbonate (783 mg, 7.39 mmol) and phenylboronic acid 362 (451 mg, 3.69 mmol), purged under argon for 30 mm. To this was added Pd(PPh3)4 (570 mg, 0.49 mmol) at RT; heated to 80 °C and stirred for 2 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mass was filtered through celite; the filtrate was diluted with water (100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were dried over sodium sulfate, filtered, concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 2percent EtOAc/ hexanes to afford compound 363 (400 mg, 35percent) as white solid. TLC: 10percent EtOAc/ hexanes (R 0.9); 1H-NMR (DMSO-d6, 400 MHz): ö 8.83 (s, 2H), 8.41-8.39 (m, 2H), 7.50-7.48 (m, 3H).

Reference: [1] Organic Letters, 2002, vol. 4, # 4, p. 513 - 516
[2] Patent: WO2009/21696, 2009, A1. Location in patent: Page/Page column 52-53
[3] Patent: US2015/349278, 2015, A1
[4] Patent: JP2016/6041, 2016, A. Location in patent: Paragraph 0250; 0251-0253
[5] Patent: US2008/64697, 2008, A1. Location in patent: Page/Page column 27
[6] Patent: US2010/75990, 2010, A1. Location in patent: Page/Page column 21
[7] Patent: WO2015/138895, 2015, A1. Location in patent: Paragraph 000296
  • 2
  • [ 100-47-0 ]
  • [ 38696-20-7 ]
YieldReaction ConditionsOperation in experiment
208.64 g
Stage #1: With sodium methylate In methanol at 20℃; for 2.00 h;
Stage #2: With ammonium chloride In methanol at 40℃; for 4.00 h;
Stage #3: With sodium methylate In methanol for 5.00 h; Reflux
101.06 g benzonitrile, 241.56g of the above-mentioned self-made N, N, N ', N' -tetramethyl-2-bromo-malondialdehydediimine hydrochlorideand methanol was added to the reaction container. The temperature was controlled to 20 °C, and 5.40 g sodium methanolatewas added to the reaction system. The reaction was continued for 2 hours. 160.47 g ammonium chloride was then added, and the reaction was continued for 4 hours at 40 °C. 64.82 g sodium methanolate was then added, and the reaction was continued at reflux for 5 hours. The solution was cooled down to room temperature. After filtering, washing, and drying, 208.64g of 2-phenyl-5-bromo-pyrimidine was obtained. The yield is 90.6percent, and HPLC purity is of 98.8percent.
Reference: [1] Patent: , 2016, . Location in patent: Paragraph 0071; 0072; 0074; 0075
  • 3
  • [ 32779-37-6 ]
  • [ 98-80-6 ]
  • [ 38696-20-7 ]
  • [ 29134-16-5 ]
Reference: [1] Organic and Biomolecular Chemistry, 2003, vol. 1, # 17, p. 3069 - 3077
  • 4
  • [ 114078-88-5 ]
  • [ 618-39-3 ]
  • [ 38696-20-7 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 31, p. 12285 - 12292
  • 5
  • [ 179260-95-8 ]
  • [ 38696-20-7 ]
  • [ 15719-64-9 ]
Reference: [1] Chemische Berichte, 1902, vol. 35, p. 3168
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