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Product Details of [ 2927-71-1 ]

CAS No. :2927-71-1 MDL No. :MFCD00233551
Formula : C4HCl2FN2 Boiling Point : -
Linear Structure Formula :- InChI Key :WHPFEQUEHBULBW-UHFFFAOYSA-N
M.W :166.97 Pubchem ID :250705
Synonyms :

Calculated chemistry of [ 2927-71-1 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 32.01
TPSA : 25.78 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 2.23
Log Po/w (WLOGP) : 2.34
Log Po/w (MLOGP) : 1.25
Log Po/w (SILICOS-IT) : 2.77
Consensus Log Po/w : 2.07

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.77
Solubility : 0.281 mg/ml ; 0.00168 mol/l
Class : Soluble
Log S (Ali) : -2.41
Solubility : 0.655 mg/ml ; 0.00392 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.16
Solubility : 0.117 mg/ml ; 0.000698 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7

Safety of [ 2927-71-1 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2927-71-1 ]

* 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 [ 2927-71-1 ]
  • Downstream synthetic route of [ 2927-71-1 ]

[ 2927-71-1 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 2927-71-1 ]
  • [ 155-10-2 ]
Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1992, vol. 62, # 6.2, p. 1122 - 1125[2] Zhurnal Obshchei Khimii, 1992, vol. 62, # 6, p. 1363 - 1366
[3] Nucleosides and Nucleotides, 1999, vol. 18, # 4-5, p. 635 - 636
[4] Patent: CN106349169, 2017, A, . Location in patent: Paragraph 0013
  • 2
  • [ 51-21-8 ]
  • [ 2927-71-1 ]
YieldReaction ConditionsOperation in experiment
95% With trichlorophosphate In <i>N</i>,<i>N</i>-dimethyl-aniline at 100℃; for 13 h; Inert atmosphere; Large scale 5-fluoropyrimidine-2,4-diol (525 kg, 1.00 mol eq) is mixed with phosphorous oxychloride (1545 kg, 2.50 mol eq) and heated to about 100° C. with stirring under a nitrogen atmosphere. N,N-dimethylaniline (980 kg, 2.00 mol eq) is then added over a period of about 9 hours and the resulting mixture stirred at about 100° C. for up to 4 hours.
This is then cooled to about 20° C. over about 2 hours and then quenched into a mixture of water (3150 kg) and dichloromethane (1915 kg), maintaining the temperature below 40° C.
The contents are then stirred at about 20° C. for at least 3 hours and then the layers separated.
The aqueous phase is washed with dichloromethane (1915 kg) and the layers again separated.
The combined organics are then washed with concentrated aqueous hydrochloric acid (525 kg) at least once, sometimes more than once, then with 5percent w/w aqueous sodium hydrogen carbonate solution (2625 kg).
The resulting organic solution is then distilled at atmospheric pressure down to about 1310 kg to give a solution of 2,4-dichloro-5-fluoro-pyrimidine in dichloromethane, with typical solution strength of about 50percent w/w and yield of about 95percent.
This solution is then used directly in the next process.
92% at 95 - 120℃; for 4 h; After the input of 5-fluoropyrimidine-2,4-diol (formula 11) 11.2g (86.1m) and phosphorus oxychloride (POCl3) 38.9g (253.8m) to the reactor and heated to 95 °C, 20.7g N,N-dimethylamine (DMA) was added dropwise for 1 hour and the temperature was raised to 120 °C, this mixture was stirred for 3 hours. Cooling the temperature to 0 °C, and the dropwise addition of 3N HCl solution in 1500ml below 10 °C. After the addition was complete, filtered and stirred for 3 hours at 10 °C and dried to give 2,4-dichloro-5-fluoropyrimidine (chemical formula 9) 13.2g (79.1mmol) (yield: 92percent).
Reference: [1] Patent: US2015/175639, 2015, A1, . Location in patent: Paragraph 0145
[2] Journal of Organic Chemistry, 2011, vol. 76, # 10, p. 4149 - 4153
[3] Patent: KR2016/69892, 2016, A, . Location in patent: Paragraph 0090-0093
[4] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 9, p. 2288 - 2300
[5] Patent: US2005/234046, 2005, A1, . Location in patent: Page/Page column 64
  • 3
  • [ 51-21-8 ]
  • [ 2927-71-1 ]
YieldReaction ConditionsOperation in experiment
94% at 95 - 120℃; for 4 h; 11.1 g (85.3 mmol) of 5-fluorouracil (Formula 10) and 39.4 g (257.0 mmol) of phosphorus oxychloride (POCl3) were added to the reactor, and the temperature was raised to 95 °C. N,N-Dimethylamine was added dropwise for 1 hour, the temperature was raised to 120 °C, and the mixture was stirred for 3 hours. The temperature was cooled to 0 °C and 1500 ml of 3N HCl aqueous solution was added dropwise at 10 °C or lower. After completion of the dropwise addition, the mixture was stirred at 10 °C for 3 hours, filtered and dried to obtain 13.4 g (80.3 mmol) of 2,4-dichloro-5-fluoropyrimidine (formula 9) (yield: 94percent)
87%
Stage #1: at 95℃; for 3.5 h;
Stage #2: With hydrogenchloride In water at 0 - 20℃;
Example 30A was also prepared as follows. Dimethylaniline (195 mL, 1.54 mol) was added to a slurry of 5-fluorouracil (99.73 g, 0.77 mol) in phosphorus oxychloride (215 mL, 2.31 mol) at 95 °C under a nitrogen atmosphere. The reaction mixture was stirred at this temperature for 3.5 h, cooled to room temperature and then slowly added to a stirred mixture of ice (200 g) and 6 M HCl (200 mL). The resulting slurry was extracted with dichloromethane (2 x 400 mL) and the combined organic extracts were washed with DI water (4 x 275 mL), dried over MgSO4 and concentrated under reduced pressure to afford 111.77 g (87percent, 98.1percent AUC by HPLC) of 5-fluoro-2,4-dichloro-pyrimidine as an amber oil. A molar solution of sodium hydroxide (1.34 L) was slowly added to a solution of the 5-fluoro-2,4-dichloro-pyrimidine (111.77 g, 0.67 mol) in THF (377 mL) at 0 °C. After the reaction mixture was stirred for about 30 min at room temperature, the pH was adjusted to 6 by a slow addition of 1.0 M HCl. The aqueous solution was extracted with ethyl acetate (440 mL) to remove impurities following which the pH was adjusted to 1 with 1.0 M HCl. The acidic aqueous solution was extracted with ethyl acetate (4 x 555 mL) and the combined organic extracts were washed with brine (111 mL), dried over MgSO4 and concentrated under reduced pressure to produce 88.35 g (89percent, 99.2percent AUC by HPLC) of 2-chloro-5-fluoro-3H-pyrimidin-4-one as an off-white powder.
87% at 95℃; for 3.5 h; Example 1a 2-Chloro-5-fluoro-3H-pyrimidin-4-one The title compound was prepared in 56percent yield from 2,4-dichloro-5-fluoro-pyrimidine as described in U.S. patent application Ser. No. 10/918,317. Specifically, 5-Fluoro-2,4-dichloro-pyrimidine was stirred in THF (10 mL) with 1N NaOH at r.t. for 3 h. The solution was made slightly acidic with 1N HCl and was extracted with CHCl3. Organics were dried (MgSO4) and concentrated in vacuo. Precipitation from 20percent CHCl3/hexanes and collection by filtration gave the title compound. 1H NMR (400 MHz, DMSO-d6): δ 13.98 (br s, 1H), 8.14 (d, 1H, J=3.2 Hz). The title compound of Example 1a was also prepared as follows. Dimethylaniline (195 mL, 1.54 mol) was added to a slurry of 5-fluorouracil (99.73 g, 0.77 mol) in phosphorus oxychloride (215 mL, 2.31 mol) at 95° C. under a nitrogen atmosphere. The reaction mixture was stirred at this temperature for 3.5 h, cooled to room temperature and then slowly added to a stirred mixture of ice (200 g) and 6 M HCl (200 mL). The resulting slurry was extracted with dichloromethane (2.x.400 mL) and the combined organic extracts were washed with DI water (4.x.275 mL), dried over MgSO4 and concentrated under reduced pressure to afford 111.77 g (87percent, 98.1percent AUC by HPLC) of 5-fluoro-2,4-dichloro-pyrimidine as an amber oil. A molar solution of sodium hydroxide (1.34 L) was slowly added to a solution of the 5-fluoro-2,4-dichloro-pyrimidine (111.77 g, 0.67 mol) in THF (377 mL) at 0° C. After the reaction mixture was stirred for about 30 min at room temperature, the pH was adjusted to 6 by a slow addition of 1.0 M HCl. The aqueous solution was extracted with ethyl acetate (440 mL) to remove impurities following which the pH was adjusted to 1 with 1.0 M HCl. The acidic aqueous solution was extracted with ethyl acetate (4.x.555 mL) and the combined organic extracts were washed with brine (111 mL), dried over MgSO4 and concentrated under reduced pressure to produce 88.35 g (89percent, 99.2percent AUC by HPLC) of 2-chloro-5-fluoro-3H-pyrimidin-4-one as an off-white powder.
85% for 1.66667 h; Reflux; Inert atmosphere Intermediate Example 3
Preparation of 2, 4-Dichloro-5-fluoropyrimidine.
To 5-fluorouracil (5.0 g, 0.04 mol) was added phosphorus oxychloride (25 mL, 0.27 mol) and N,N-diethylaniline (6 mL, 0.06 mol) while stirring at room temperature.
After being heated under reflux for 100 min, the mixture was concentrated under reduced pressure.
The residue was poured into ice water (100 mL) and extracted with ether.
The organic layer was dried with sodium sulfate and evaporated at 0 °C under reduced pressure to give 5.35 g of the desired product (85percent).
Mp 37-38 °C. HNMR: δ 8.95 (s, 1H).
84% at 20℃; Reflux To a stirred mixture of 5-fluoropyrimidine-2,4(1 H,3H)-dione (3.0 g, 23 mmol) and phosphorous pentachloride (14.41 g, 69 mmol) was added phosphorous oxychloride (12.6 mL, 130 mmol). The reaction mixture was heated to reflux, stirred 5 hours and then cooled to ambient temperature and stirred overnight. The mixture was carefully poured onto ice/water (600 mL) and stirred for 1 hour. Sodium chloride was added and the product was extracted into dichloromethane. The combined organic layer was dried (MgS0 ), filtered and evaporated to give the title compound (84percent) as a yellow solid.LRMS (m/z): 167 (M+1)+.1H-NMR δ (CDCI3): 8.49 (s, H)
84% for 5 h; Reflux   5-fluoropyrimidine-2,4(1H,3H)-dione (3.0 g, 23 mmol) and   phosphorous pentachloride (14.41 g, 69 mmol) was added   phosphorous oxychloride (12.6 mL, 130 mmol). The reaction mixture was heated to reflux, stirred 5 hours and then cooled to ambient temperature and stirred overnight. The mixture was carefully poured onto ice/   water (600 mL) and stirred for 1 hour.   Sodium chloride was added and the product was extracted into dichloromethane. The combined organic layer was dried (MgSO4), filtered and evaporated to give the   title compound (84percent) as a yellow solid.LRMS (m/z): 167 (M+1)+.1H-NMR δ (CDCl3): 8.49 (s, 1 H)
84% at 20℃; Reflux PREPARATION 212,4-Dichloro-5-fluoropyrimidineTo a stirred mixture of 5-fluoropyrimidine-2,4(1 /-/,3/-/)-dione (3.0 g, 23 mmol) and phosphorous pentachloride (14.41 g, 69 mmol) was added phosphorous oxychloride (12.6 mL, 130 mmol). The reaction mixture was stirred and heated to reflux for 5 hours and then cooled to ambient temperature and stirred overnight. The mixture was carefully poured onto ice/water (600 mL) and then stirred for 1 hour. Sodium chloride was added and the product was extracted into dichloromethane. The combined organic layer was dried (MgS04), filtered and evaporated to give the title compound (84percent) as a yellow solid.LRMS (m/z): 167 (M+1 )+.1H-NMR δ (CDCIs): 8.49 (s, 1 H).
84% for 5 h; Reflux To a stirred mixture of 5-fluoropyrimidine-2,4(1H,3H)-dione (3.0 g, 23 mmol) and phosphorous pentachloride (14.41 g, 69 mmol) was added phosphorous oxychloride (12.6 mL, 130 mmol).
The reaction mixture was heated to reflux, stirred 5 hours and then cooled to ambient temperature and stirred overnight.
The mixture was carefully poured onto ice/water (600 mL) and stirred for 1 hour.
Sodium chloride was added and the product was extracted into dichloromethane.
The combined organic layer was dried (MgSO4), filtered and evaporated to give the title compound (84percent) as a yellow solid.
LRMS(m/z): 167(M+1)+.
1H-NMR δ (CDCl3): 8.49 (s, 1H).
50% for 3 h; Reflux A mixture of 15.6 g of 5-FU [1] in 80 mL of POCl3 was stirred in a three neck-flask equipped with condenser, thermometer and dropping funnel at 40° C. After addition of 25 mL of N,N-dimethylaniline drop wise, the resulting mixture was heated to reflux for 3 hours. The excess of POCl3 was evaporated under reduced pressure. The mixture was cooled to room temperature and poured into 75 g of crushed ice. It was then extracted with chloroform (50 mL three times). The combined extracts were washed with water, dried with MgSO4, and concentrated to give a yellowish solid of compound [7] in about 50percent yield.

Reference: [1] Patent: KR2016/69892, 2016, A, . Location in patent: Paragraph 0067-0070
[2] J. Gen. Chem. USSR (Engl. Transl.), 1992, vol. 62, # 6.2, p. 1122 - 1125[3] Zhurnal Obshchei Khimii, 1992, vol. 62, # 6, p. 1363 - 1366
[4] Patent: EP1506967, 2005, A1, . Location in patent: Page/Page column 67
[5] Patent: US2007/66636, 2007, A1, . Location in patent: Page/Page column 19; 20
[6] Patent: EP2311825, 2015, B1, . Location in patent: Paragraph 0162; 0163
[7] Patent: WO2011/76419, 2011, A1, . Location in patent: Page/Page column 112
[8] Patent: EP2338888, 2011, A1, . Location in patent: Paragraph 0144; 0145
[9] Patent: WO2013/17461, 2013, A1, . Location in patent: Page/Page column 82
[10] Patent: EP2554544, 2013, A1, . Location in patent: Paragraph 0153
[11] Patent: US9551724, 2017, B2, . Location in patent: Page/Page column 15; 16; 19
[12] Tetrahedron Letters, 1997, vol. 38, # 7, p. 1111 - 1114
[13] Nucleosides and Nucleotides, 1999, vol. 18, # 4-5, p. 635 - 636
[14] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 18, p. 2961 - 2966
[15] Patent: US2006/58525, 2006, A1, . Location in patent: Page/Page column 17-18
[16] Patent: US2002/165241, 2002, A1,
[17] Patent: US2002/165241, 2002, A1,
[18] Patent: US6586594, 2003, B1,
[19] Patent: US5998436, 1999, A,
[20] Patent: US5278175, 1994, A,
[21] Patent: WO2008/91681, 2008, A2, . Location in patent: Page/Page column 199; 235
[22] Patent: US2009/238808, 2009, A1,
[23] Patent: US2010/16298, 2010, A1, . Location in patent: Page/Page column 168
[24] Journal of Medicinal Chemistry, 2011, vol. 54, # 2, p. 510 - 524
[25] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 5, p. 1349 - 1354
[26] Organic Process Research and Development, 2001, vol. 5, # 1, p. 28 - 36
[27] Patent: US2015/266828, 2015, A1, . Location in patent: Paragraph 0312
[28] Patent: CN106349169, 2017, A, . Location in patent: Paragraph 0013
  • 4
  • [ 6693-08-9 ]
  • [ 2927-71-1 ]
Reference: [1] Journal of Fluorine Chemistry, 1989, vol. 45, p. 417 - 430
  • 5
  • [ 74-96-4 ]
  • [ 2927-71-1 ]
Reference: [1] Patent: US6586594, 2003, B1,
  • 6
  • [ 2927-71-1 ]
  • [ 155-12-4 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With sodium hydroxide In tetrahydrofuran at 0 - 20℃; for 0.5 h;
Stage #2: With hydrogenchloride In tetrahydrofuran
Example 30A was also prepared as follows. Dimethylaniline (195 mL, 1.54 mol) was added to a slurry of 5-fluorouracil (99.73 g, 0.77 mol) in phosphorus oxychloride (215 mL, 2.31 mol) at 95 °C under a nitrogen atmosphere. The reaction mixture was stirred at this temperature for 3.5 h, cooled to room temperature and then slowly added to a stirred mixture of ice (200 g) and 6 M HCl (200 mL). The resulting slurry was extracted with dichloromethane (2 x 400 mL) and the combined organic extracts were washed with DI water (4 x 275 mL), dried over MgSO4 and concentrated under reduced pressure to afford 111.77 g (87percent, 98.1percent AUC by HPLC) of 5-fluoro-2,4-dichloro-pyrimidine as an amber oil. A molar solution of sodium hydroxide (1.34 L) was slowly added to a solution of the 5-fluoro-2,4-dichloro-pyrimidine (111.77 g, 0.67 mol) in THF (377 mL) at 0 °C. After the reaction mixture was stirred for about 30 min at room temperature, the pH was adjusted to 6 by a slow addition of 1.0 M HCl. The aqueous solution was extracted with ethyl acetate (440 mL) to remove impurities following which the pH was adjusted to 1 with 1.0 M HCl. The acidic aqueous solution was extracted with ethyl acetate (4 x 555 mL) and the combined organic extracts were washed with brine (111 mL), dried over MgSO4 and concentrated under reduced pressure to produce 88.35 g (89percent, 99.2percent AUC by HPLC) of 2-chloro-5-fluoro-3H-pyrimidin-4-one as an off-white powder.
72% With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 3 h; To a solution of 5-fluoro-2,4-dichloro-pyrimidine (1 g, 5.99mmol) in THF (3.3 mL) was added NaOH (1 M in water, 11.7 mL) at 0 °C. The reaction mixture was stirred at room temperature for 3 h before it was acidified (pH 1) with 1 M HCl. The product was extracted with EtOAc (3x10 mL), the combined organic extracts were dried over Na2SO4 and the solvent was removed under reduced pressure providing crude 84 (638 mg, 72percent), which was used for the next step without further purification.
56%
Stage #1: With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 0.5 - 3 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water
Example 1a 2-Chloro-5-fluoro-3H-pyrimidin-4-one The title compound was prepared in 56percent yield from 2,4-dichloro-5-fluoro-pyrimidine as described in U.S. patent application Ser. No. 10/918,317. Specifically, 5-Fluoro-2,4-dichloro-pyrimidine was stirred in THF (10 mL) with 1N NaOH at r.t. for 3 h. The solution was made slightly acidic with 1N HCl and was extracted with CHCl3. Organics were dried (MgSO4) and concentrated in vacuo. Precipitation from 20percent CHCl3/hexanes and collection by filtration gave the title compound. 1H NMR (400 MHz, DMSO-d6): δ 13.98 (br s, 1H), 8.14 (d, 1H, J=3.2 Hz). The title compound of Example 1a was also prepared as follows. Dimethylaniline (195 mL, 1.54 mol) was added to a slurry of 5-fluorouracil (99.73 g, 0.77 mol) in phosphorus oxychloride (215 mL, 2.31 mol) at 95° C. under a nitrogen atmosphere. The reaction mixture was stirred at this temperature for 3.5 h, cooled to room temperature and then slowly added to a stirred mixture of ice (200 g) and 6 M HCl (200 mL). The resulting slurry was extracted with dichloromethane (2.x.400 mL) and the combined organic extracts were washed with DI water (4.x.275 mL), dried over MgSO4 and concentrated under reduced pressure to afford 111.77 g (87percent, 98.1percent AUC by HPLC) of 5-fluoro-2,4-dichloro-pyrimidine as an amber oil. A molar solution of sodium hydroxide (1.34 L) was slowly added to a solution of the 5-fluoro-2,4-dichloro-pyrimidine (111.77 g, 0.67 mol) in THF (377 mL) at 0° C. After the reaction mixture was stirred for about 30 min at room temperature, the pH was adjusted to 6 by a slow addition of 1.0 M HCl. The aqueous solution was extracted with ethyl acetate (440 mL) to remove impurities following which the pH was adjusted to 1 with 1.0 M HCl. The acidic aqueous solution was extracted with ethyl acetate (4.x.555 mL) and the combined organic extracts were washed with brine (111 mL), dried over MgSO4 and concentrated under reduced pressure to produce 88.35 g (89percent, 99.2percent AUC by HPLC) of 2-chloro-5-fluoro-3H-pyrimidin-4-one as an off-white powder.
Reference: [1] Patent: EP1506967, 2005, A1, . Location in patent: Page/Page column 67
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 18, p. 4984 - 4995
[3] Patent: US2007/66636, 2007, A1, . Location in patent: Page/Page column 19; 20
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 2, p. 510 - 524
[5] Patent: US2007/60529, 2007, A1, . Location in patent: Page/Page column 14
[6] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 5, p. 1349 - 1354
  • 7
  • [ 2927-71-1 ]
  • [ 62802-42-0 ]
YieldReaction ConditionsOperation in experiment
50% With acetic acid; zinc In tetrahydrofuran at 70℃; for 6 h; Heating / reflux Step A: 2-Chloro-5-fluoropyrimidine To 2,4-dichloro-5-fluoropyrimidine (15.0 g, 89.8 mmol) is added tetrahydrofuran (100 mL) and zinc powder (17.6 g, 269 mmol). The mixture is heated to 70 0C with vigorous stirring, acetic acid (5.14 mL, 89.8 mmol) is added over Ih and the mixture is heated at reflux for an additional 5h. The mixture is diluted with dichloromethane, filtered <n="94"/>through celite, evaporated in vacuo and purified on silica gel to give the desired product (6.00 g, 50 percent).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 5, p. 1376 - 1381
[2] Patent: WO2007/106705, 2007, A1, . Location in patent: Page/Page column 92-93
[3] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1985, vol. 39, # 8, p. 691 - 696
[4] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 9, p. 2288 - 2300
[5] Organic Preparations and Procedures International, 1995, vol. 27, # 5, p. 600 - 602
[6] Patent: US2002/165241, 2002, A1,
[7] Patent: US2002/165241, 2002, A1,
[8] Patent: US2005/234046, 2005, A1, . Location in patent: Page/Page column 64
[9] Patent: WO2013/142269, 2013, A1, . Location in patent: Paragraph 0639; 0640; 0641
  • 8
  • [ 75-16-1 ]
  • [ 2927-71-1 ]
  • [ 134000-96-7 ]
YieldReaction ConditionsOperation in experiment
48% at 0℃; for 0.5 h; To a solution of 2,4-dichloro-5-fluoropyrimidine (1 .02 g, 6.08 mmol) inTHF/NMP (38 mL/3 mL) was added Fe(acac)3 (215 mg, 0.61 mmol) and the mixture was cooled to 0 °C. 3.0 M methylmagnesium bromide in Et2O (3.04 mL, 9.12 mmol) was added dropwise. After 30 min at 0 °C, the reaction was complete and quenched with saturated aqueous NH CI solution. Et2O was added and the layers were separated and the aqueous layer was further extracted with several portions of Et2O. The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. Chromatography (Hexanes to 10percent EtOAc/Hexanes) gave the desired product as a waxy white solid (430 mg, 48percent). 1H NMR (400 MHz, CDCI3): 8.35 (s, 1 H), 2.55 (d, J = 2.5 Hz, 3H).
48% at 0℃; for 0.5 h; To a solution of 2,4-dichloro-5-fluoropyrimidine (1 .02 g, 6.08 mmol) inTHF/NMP (38 mL/3 ml_) was added Fe(acac)3 (215 mg, 0.61 mmol) and the mixture was cooled to 0 oC. 3.0 M methylmagnesium bromide in Et2O (3.04 ml_, 9.12 mmol) was added dropwise. After 30 min at 0 oC, the reaction was complete and quenched with saturated aqueous NH CI solution. Et2O was added and the layers were separated and the aqueous layer was further extracted with several portions of Et2O. The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. Chromatography (Hexanes to 10percent EtOAc/Hexanes) gave the desired product as a waxy white solid (430 mg, 48percent). 1H NMR (400 MHz, CDCI3): 8.35 (s, 1 H), 2.55 (d, J = 2.5 Hz, 3H).
48% at 0℃; Intermediate 55: 2-Chloro-5-fluoro-4-methylpyrimidine.To a solution of 2,4-dichloro-5-fluoropyrimidine (1 .02 g, 6.08 mmol) inTHF/NMP (38 mL/3 mL) was added Fe(acac)3 (215 mg, 0.61 mmol) and the mixture was cooled to 0 °C. 3.0 M methylmagnesium bromide in Et20 (3.04 mL, 9.12 mmol) was added dropwise. After 30 min at 0 °C, the reaction was complete and quenched with saturated aqueous NH4CI solution. Et20 was added and the layers were separated and the aqueous layer was further extracted with several portions of Et20. The combined organic extracts were dried over Na2S04, filtered and concentrated in vacuo. Chromatography (Hexanes to 10percent EtOAc/Hexanes) gave the desired product as a waxy white solid (430 mg, 48percent). 1H NMR (400 MHz, CDCI3): 8.35 (s, 1 H), 2.55 (d, J = 2.5 Hz, 3H).
42.4% With acetylacetone iron (III) salt In tetrahydrofuran; ethanol at 0℃; To a solution of 2,4-dichloro-5-fluoropyrimidine (5 g, 29.9 mmol) in THF (200mL) was added acetylacetone iron (III) salt (1.058 g, 2.99 mmol) and the reaction mixturewas cooled to 0 °C. Methylmagnesium bromide in Et20 (14.97 mL, 44.9 mmol) was added dropwise at the same temperature. After 30 mm, the reaction was completed and quenched with saturated aqueous NH4C1 solution. Diethyl ether was added and the layers were separated and the aqueous layer was further extracted with several portions of Et20.The combined organic phases were dried over sodium sulfate, filtered and the solvent was removed under vacuum. The desired product, 2-chloro-5-fluoro-4-methylpyrimidine (1.9 g, 12.70 mmol, 42.4 percent yield) was isolated as a white solid by ISCO (40g silica gel, liquid loading, 0-5percent ethylacetate/pet ether).

Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 8, p. 3263 - 3282
[2] Patent: WO2011/50200, 2011, A1, . Location in patent: Page/Page column 84
[3] Patent: WO2011/50198, 2011, A1, . Location in patent: Page/Page column 74
[4] Patent: WO2012/145581, 2012, A1, . Location in patent: Page/Page column 74
[5] Patent: WO2015/89143, 2015, A1, . Location in patent: Page/Page column 95
  • 9
  • [ 2927-71-1 ]
  • [ 134000-96-7 ]
YieldReaction ConditionsOperation in experiment
48% With methylmagnesium bromide In tetrahydrofuran; NMP (N-methylpyrrolidone); diethyl ether at 0℃; for 0.5 h; Int rmediate 32: 2-Chloro-5-fluoro-4-methylpyrimidine.To a solution of 2,4-dichloro-5-fluoropyrimidine (1 .02 g, 6.08 mmol) inTHF/NMP (38 mL/3 mL) was added Fe(acac)3 (215 mg, 0.61 mmol) and the mixture was cooled to 0 C. 3.0 M methylmagnesium bromide in Et2O (3.04 mL, 9.12 mmol) was added dropwise. After 30 min at 0 C, the reaction was complete and quenched with saturated aqueous NH4CI solution. Et2O was added and the layers were separated and the aqueous layer was further extracted with several portions of Et2O. The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. Chromatography (Hexanes to 10percent EtOAc/Hexanes) gave the desired product as a waxy white solid (430 mg, 48percent). 1H NMR (400 MHz, CDCI3): 8.35 (s, 1 H), 2.55 (d, J = 2.5 Hz, 3H).
Reference: [1] Patent: WO2011/50202, 2011, A1, . Location in patent: Page/Page column 69-70
  • 10
  • [ 676-58-4 ]
  • [ 2927-71-1 ]
  • [ 134000-96-7 ]
YieldReaction ConditionsOperation in experiment
51% With iron(III) acetylacetonate In tetrahydrofuran at 0℃; for 130 h; Example 131A2-chloro-5-fluoro-4-methylpyrimidineA solution of 2,4-dichloro-5-fluoropyrimidine (2.5 g, 14.97 mmol) and iron(III) acetylacetonate (1.058 g, 2.99 mmol) in THF (100 mL) and NMP (10 mL) was chilled below 0° C. and methyl magnesium chloride (5.99 mL, 18.0 mmol, 3.0 M solution in THF) was added dropwise over 10 minutes. After stirring for 2 hours at 0° C., the mixture was quenched with 200 mL saturated NH4Cl and extracted twice with 200 mL EtOAc. The combined organic extracts were washed with 200 mL saturated NH4Cl and 200 mL brine, dried over Na2SO4 and concentrated. Purification by chromatography (Grace Reveleris 80 g column, eluted with 0-20percent EtOAc/heptane, 35 mL/min) provided the title compound (1.13 g, 7.70 mmol, 51percent yield). GC/MS (EI+) m/z 146.0 (M+); 1H NMR (400 MHz, CDCl3) δ 8.36 (s, 1H), 2.55 (d, J=2.5, 3H); 13C NMR (101 MHz, CDCl3) δ 158.78, 158.61, 157.34, 154.92, 154.89, 154.74, 145.86, 145.63, 17.74, 17.73.
Reference: [1] Patent: US2012/245124, 2012, A1, . Location in patent: Page/Page column 56-57
  • 11
  • [ 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
  • 12
  • [ 1231930-37-2 ]
  • [ 2927-71-1 ]
  • [ 1231930-42-9 ]
YieldReaction ConditionsOperation in experiment
86% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In acetonitrile at 85℃; for 8 h; Inert atmosphere To a suspension of 4-fluoro-l-isopropyl-2-methyl-6-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-lH-benzo[d]imidazole (2-16, 318 nig, 1 mmol), 2,4-dichloro-5- fluoropyrimidine (2-17, 166 mg, 1 mmol), and Pd(PPrn)4 (115.6 mg, 0.1 mmol) in 6 mL of CH3CN was added 2 ml, of saturated Na2C03 under an atmosphere of N2. The mixture was heated to 85 °C and stirred for 8h. Then the reaction was cooled to room temperature, extracted with CHCh and isopropanol (V/V=4: 1) and the combined organic layers were washed with brine, dried over anhydrous Na2S€>4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (0-10percent MeOH in DCM) to give 6-(2-cUoro-5-fluoropyrimidin-4-yl)-4-fluoro-l-isopropyl-2-methyl IH-benzoj djirnidazole 2-18 as a gray solid (277 mg, 86percent). LCMS: m/z 323.1 [M+l].
66%
Stage #1: With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water at 80℃; Inert atmosphere
Stage #2: at 80℃; for 5.5 h; Inert atmosphere
To a 250 mL 3-neck round bottom flask equipped with a N2 inlet, overhead stirrer, reflux condenser and temperature probe was charged 5-fluoro-2,4-dichloropyrimidine (2, 5.17 g,31.0 mmol, 1.4 equiv), Na2CO3 (5.86 g, 55.3 mmol, 2.5 equiv), water (9 mL), and DME (45 mL). The solution was degassed by sparging N2 subsurface for 30 min. After subsurface sparging, PdCl2(PPh3)2 (46.6 mg, 66 lmol, 0.03 equiv) was added in one portion. The resulting solution was heated to 80 C. In a separate 100 mL round bottom flask was charged boronic ester 3 (7.04 g, 22.1 mmol,1.0 equiv) and DME (40 mL). The resulting solution was added to the heated solution by syringe pump over the course of 1.5 h. After all of boronic ester 3 was added, the reaction solution was stirred at 80 C for an additional 4 h, at which time the reaction was complete as judged by HPLC analysis. The reaction mixture was then cooled to ambient temperature and diluted with ice cold water (300 mL) and stirred for 25 min. The resulting slurry was collected by filtration and the resulting wetcake was slurried in IPA (105 mL) and heated to 80 C for 3.5 h. The heated slurry was then allowed to cool to ambient temperature over 16 h and the solid was collected by filtration and washed with IPA (35 mL). The wetcake was dried in a vacuum oven at 45 C for 18 h to obtain the desired biaryl compound 6 in 66percent yield. Compound 6: IR (film)mmax = 3413, 2972, 2940, 2892, 1567, 1507, 1401, 1388, 1348, 1210 cm1; 1HNMR (500 MHz, CDCl3): d = 8.50 (d, J = 3.4 Hz, 1H), 8.15 (d, J = 1.2 Hz, 1H), 7.77(d, J = 11.7 Hz, 1H), 4.74 (septet, J = 7.0 Hz, 1H), 2.69 (s, 3H), 1.69 (d, J = 7.0 Hz, 6H) ppm; 13C NMR (125 MHz, CDCl3): d = 155.3, 154.8, 154.2, 153.9, 153.2,148.4, 136.6, 134.7, 125.5, 108.8, 108.2, 48.7, 21.5, 15.2 ppm; HR-MS [ESI]:Calcd for C15H14N4ClF2 [M+H+]: 323.0870, found 323.0864.
14.4 g With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water at 80 - 84℃; for 1 h; Inert atmosphere Bubble nitrogen into a mixture of 2,4-dichloro-5-fluoro-pyrimidine (12.7 g), bis(triphenylphosphine)palladium(II) chloride (4.9 g), sodium carbonate 2 M in water (103.7 mL) and 1 ,2-dimethoxyethane (120 mL). Heat in a pre-heated oil bath at 80 °C and add drop wise a solution of 4-fluoro-l-isopropyl-2-methyl-6-(4,4,5,5-tetramethyl- [l,3,2]dioxaborolan-2-yl)-lH-benzoimidazole (22 g) in 1,2-dimethoxy ethane (200 mL). Stir the mixture at 84 °C for 1 hour. Cool to room temperature, add ethyl acetate (800 mL) and wash twice with brine (100 mL). Dry over magnesium sulfate and remove the solvent under vacuum. Triturate with acetonitrile to afford 14.4 g of the title compound. (0098) MS (ES+): m/z= 323 (M+H)+.
13.18 g With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water at 85℃; for 1 h; Inert atmosphere The compound of formula XXII-1 (9.95 g, 59.60 mmol) was dissolved in ethylene glycol dimethyl ether (210 mL) and 2MAqueous solution of sodium carbonate (140 mL), compound of formula XVII-1 (17.5 g, 54.18 mmol),Bis (triphenylphosphine) palladium chloride (1.0 g).Nitrogen exchange reaction bottle of air, open the oil bath heating, stirring at 85C 1h. The reaction flask was cooled to roomThe reaction solution was poured into 300mL of water, a large number of solid precipitation, vacuum filtration after the full stirring, the filter cake was dried gray-white solidBody 13.18g
5 g With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water at 80 - 84℃; for 1 h; Inert atmosphere Under N2 atmosphere, 2,4-dichloro-5-fluoro-pyrimidine (6.3 g), commercially available, was dissolved in 1,2-dimethoxyethane (60 mL). Bis(triphenylphosphine)palladium(II) chloride (2.5 g) and 2M aqueous sodium carbonate solution (50 mL) were then added. Mixed solution was dropped at 80 °C4-fluoro-1-isopropyl-2-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolane-2-yl) -1H-benzimidazole(10 g) 1,2-dimethoxyethane (50 mL) solution. The reaction was stirred at 84 °C for 1 hour and the reaction was monitored by TLC. Cooled to room temperature, the resulting mixture was extracted with EtOAc (40 mL X 3) and the combined organic phases were washed with saturated brine (40 mL X 3). After drying over anhydrous sodium sulfate, the crude product was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to obtain the target Compound (5g).
2.6 g With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water at 80℃; for 4 h; 2.3 g of 2,4-dichloro-5-fluoropyrimidine was dissolved in 20 ml of ethylene glycol dimethyl ether and added with an aqueous solution of sodium carbonate (4 g) and 0.9 g of Pd(PPh3)2Cl2, and heated to 80 ° C with stirring.Add 3.9g to the solution.4-Fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole-6-boronic acid pinacol ester in ethylene glycol dimethyl ether solution, maintained at 80 ° C for 4 h,The heating was stopped, and 50 ml of ethyl acetate was added thereto, and the mixture was stirred to room temperature. The reaction mixture was washed with brine and dried over anhydrous magnesium sulfate.Concentrated to give an oily material which was purified6-(2-Chloro-5-fluoropyrimidin-4-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole 2.6 g as a pale yellow solid.

Reference: [1] Patent: WO2017/185031, 2017, A1, . Location in patent: Page/Page column 96
[2] Tetrahedron Letters, 2015, vol. 56, # 7, p. 949 - 951
[3] Patent: US2010/160340, 2010, A1, . Location in patent: Page/Page column 11
[4] Patent: WO2015/130540, 2015, A1, . Location in patent: Page/Page column 22-23
[5] Patent: CN107266421, 2017, A, . Location in patent: Paragraph 0043; 0052; 0053
[6] Patent: CN104892580, 2018, B, . Location in patent: Paragraph 0064; 0065; 0066in
[7] Patent: CN107827875, 2018, A, . Location in patent: Paragraph 0051; 0052; 0054
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