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[ CAS No. 954220-98-5 ] {[proInfo.proName]}

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CAS No. 954220-98-5, is a pyrimidines compound, with a molecular weight of 181.00, molecular formula C5H3Cl2FN2, Ambeed provides reports for batches of (such as NMR, HPLC/GC).

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Chemical Structure| 954220-98-5
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Product Details of [ 954220-98-5 ]

CAS No. :954220-98-5 MDL No. :MFCD09863051
Formula : C5H3Cl2FN2 Boiling Point : -
Linear Structure Formula :- InChI Key :IYGLMCCNOPCDCR-UHFFFAOYSA-N
M.W : 181.00 Pubchem ID :24903513
Synonyms :

Safety of [ 954220-98-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 954220-98-5 ]

* 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.

  • Upstream synthesis route of [ 954220-98-5 ]
  • Downstream synthetic route of [ 954220-98-5 ]

[ 954220-98-5 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 954220-98-5 ]
  • [ 124-41-4 ]
  • [ 1192479-35-8 ]
YieldReaction ConditionsOperation in experiment
100% at 0 - 25℃; for 1 h; To a solution of A2 (R7 = F, R8 = Me, 563 mg, 3.11 mmol) in THF (6 ml_) was added 25percent sodium methoxide in MeOH (671 mg) while cooling at 0 0C. The resulting solution was slowly warmed to room temperature over 1 hr and then diluted with water and extracted with EtOAc. The EtOAc extract was concentrated and the residue was purified by silica gel column chromatography (EtOAc / hexanes) to provide A3 (R6 = MeO, R7 = F and R8 = Me) in quantitative yield.
87% at 0 - 20℃; for 1 h; Sodium methoxide (446.53 mg, 8.27 mmol) is added portion wise to a stirred solution of 2,4-dichloro-5-fluoro-6-methyl-pyrimidine (1.7 g, 7.51 mmol) in methanol (8 mL, 197.66 mmol) at 0 °C. The mixture is then stirred at room temperature for 1 hour. Water (20 mL) is added to the reaction mixture followed by dichloromethane. The layers are separated and the aqueous layer is re-extracted with dichloromethane. The combined organic extracts are dried over magnesium sulfate and the solvents are evaporated under reduced pressure to give an 8:1 of mixture of product to starting material. The crude material is purified by silica gel chromatography using a 0-99percent gradient of dichloromethane in iso-hexanes to give the title compound (1.16 g, 87percent). (CDC13) δ 4.09 (s, 3H), 2.45 (d, 3H)
52% at 0 - 20℃; for 0.5 h; Step 2 To 28 (25 g, 138 mmol) in THF (250 mL) at 0 °C was added 30 g of a 25percent/wt NaO e in methanol solution (138 mmol). Allowed to warm to room temperature over 30 minutes. Concentrated the reaction in vacuo. Purified the residue by silica gel chromatography (0-20percent acetone/hexane over 20 minutes) to provide 29 (12. 6 g, 52percent).
Reference: [1] Patent: WO2009/131974, 2009, A1, . Location in patent: Page/Page column 88
[2] Patent: WO2014/66132, 2014, A1, . Location in patent: Page/Page column 16-17
[3] Patent: WO2012/138590, 2012, A1, . Location in patent: Page/Page column 71-72
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3231 - 3248
  • 2
  • [ 67-56-1 ]
  • [ 954220-98-5 ]
  • [ 1192479-35-8 ]
YieldReaction ConditionsOperation in experiment
5.68 g With sodium methylate In tetrahydrofuran; methanol at 0℃; for 0.166667 h; Inert atmosphere To a solution of 2,4-dichloro-5-fluoro-6-methylpyrimidine (16.8 g;crude material) in dry tetrahydrofuran (170 ml) at 0°C under nitrogen was added dropwise 25percentw/w sodium methoxide in methanol (21 ml equivalent to ~5g). After ten minutes at 0°C, the reaction mixture was poured into water (500 ml) and extracted with diethyl ether (250 ml). The organic layer was washed with water then dried (MgS04) and evaporated and the residue purified by preparative HPLC. The pure fractions werecombined, aqueous saturated sodium bicarbonate added and the aqueous extracted with diethyl ether. The organic layer was washed with water and then dried (MgSC"4) and carefully evaporated to afford the title compound (5.68 g) as a white crystalline solid. LCMS (Method A2): Rt 1.11 min, m/z 177/179 [M+H]+. 1H-NMR (400 MHz, CDC13) δ (ppm): 2.44 (d, J=2.93 Hz, 3 H) 4.08 (s, 3 H)
Reference: [1] Patent: WO2014/13076, 2014, A1, . Location in patent: Page/Page column 43; 44
  • 3
  • [ 75-16-1 ]
  • [ 2927-71-1 ]
  • [ 954220-98-5 ]
YieldReaction ConditionsOperation in experiment
74%
Stage #1: at 15℃;
Stage #2: With triethylamine In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether at 0 - 5℃;
Stage #3: With iodine In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether
A literature procedure was adapted (M. Butters, J. Ebbs, S. P. Green, J. MacRae, M. C. Morland, C. W. Murtiashaw and A. J. Pettman Organic Process Research Development 2001, 5, 28-36). To a solution of 3.0 M MeMgBr in Et&2O (15 ml_, 45 mmol, 1.5 equiv.) in THF (20 ml_) was added a solution of A1 (R7 = F, 5 g, 30 mmol, 1 equiv.) in DME (20 ml_) while maintaining the temperature below 15 0C. The resulting solution was stirred at 15 0C for 1 hour and then was cooled to 0 0C. A solution Of Et3N (4.17 ml_, 30 mmol, 1 equiv.) in THF (10 ml_) was added slowly to the reaction mixture maintaining the internal temperature ~ 5 0C, then a solution of iodine (30 mmol, 1 equiv.) in THF (10 ml_) was added. The reaction mixture was quenched with water, warmed to room temperature, extracted with EtOAc and concentrated. The crude product was purified by silica gel column chromatography (CH2CI2 / hexanes) to afford A2 (R8 = Me, R7 = F) in 74percent yield.
64%
Stage #1: at 0 - 15℃; for 1.16667 h;
Stage #2: With iodine; triethylamine In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether at 5 - 15℃; for 0.5 h;
Preparation of 2-chloro-5-fluoro-4-methoxy-6-methylpyrimidineScheme 3Step 1 A solution of 2,4-dichIoro-5-fluropyrimidine 27 ( 10 g, 60 mmol) in DME (30 mL) was added to a solution of methyl magnesium bromide (3 M in ether/30 mL/1.5 equiv) in THF (30 mL) at 0 °C over 10 minutes. The reaction was stirred at 10-15 °C for 1 h and then cooled to 0 °C. Triethyl amine (8.3 mL, 1 equiv) in THF (16 mL) was added to the reaction mixture while keeping the reaction temperatur below 5 °C. Iodine (15.2 g, 1 equiv) in THF (24 mL) was then added dropwise keeping the temperature below 15 °C. The reaction was stirred for 30 minutes and water was added ( 150 mL). The pH was adjusted to pH =1 by the addition of aqueous 5N HC1. The mixture was extracted with EtOAc. The combined organics were washed with 2percent aqueous sodium bisulfite and brine. The organic layer was dried Na2S04), filtered, and concentrated in vacuo. The resulting solid was purified by silica gel chromatography (0-8percent EtOAc hex over 30 minutes) to provide 28 (6.75 g, 64percent).
32% With iodine; triethylamine In tetrahydrofuran; 1,2-dimethoxyethane at 15℃; for 1 h; Into a 250-mL 3 -necked round-bottom flask was placed bromo(methyl) magnesium (6 mL, 1.50 equiv), oxolane ( 10 mL), 2,4-dichloro-5-fluoropyrimidine (2 g, 1 1.98 mmol , 1 .00 equiv), ethylene glycol dimethyl ether (10 mL), TEA (2 mL), and diiodane (3 g, 1 1.82 mmol, 1.00 equiv). The resulting solution was stirred for I h at 15 °C. The resulting solution was allowed to react, with stirring, for an additional 1 min while the temperature was maintained at -5 °C in an ice/salt bath . The reaction was then quenched by the addition of 100 mL of water. The resulting solution was extracted with 3x100 mL of ethyl acetate and the organic layers combined. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :5). This resulted in 700 mg (32percent) of the title compound as a yellow oil. LC-MS: (ES, m/z): RT = 0.84 min, LCMS 15 : m/z = 181 [M+l].
Reference: [1] Patent: WO2009/131974, 2009, A1, . Location in patent: Page/Page column 88
[2] Patent: WO2012/138590, 2012, A1, . Location in patent: Page/Page column 71
[3] Patent: WO2018/118842, 2018, A1, . Location in patent: Paragraph 0505-0508
[4] Patent: WO2014/13076, 2014, A1, . Location in patent: Page/Page column 43
[5] Patent: WO2014/66132, 2014, A1, . Location in patent: Page/Page column 16
[6] Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3231 - 3248
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