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Chemical Structure| 14080-23-0
Chemical Structure| 14080-23-0
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Product Details of [ 14080-23-0 ]

CAS No. :14080-23-0 MDL No. :MFCD00160513
Formula : C5H3N3 Boiling Point : -
Linear Structure Formula :- InChI Key :IIHQNAXFIODVDU-UHFFFAOYSA-N
M.W : 105.10 Pubchem ID :2757979
Synonyms :

Calculated chemistry of [ 14080-23-0 ]

Physicochemical Properties

Num. heavy atoms : 8
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 : 26.75
TPSA : 49.57 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.16 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.11
Log Po/w (XLOGP3) : -0.31
Log Po/w (WLOGP) : 0.35
Log Po/w (MLOGP) : -1.08
Log Po/w (SILICOS-IT) : 0.92
Consensus Log Po/w : 0.2

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.85
Solubility : 14.8 mg/ml ; 0.141 mol/l
Class : Very soluble
Log S (Ali) : -0.27
Solubility : 56.4 mg/ml ; 0.536 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.67
Solubility : 2.26 mg/ml ; 0.0215 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 14080-23-0 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P280-P301+P310 UN#:3439
Hazard Statements:H301-H317 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 14080-23-0 ]

* 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 [ 14080-23-0 ]
  • Downstream synthetic route of [ 14080-23-0 ]

[ 14080-23-0 ] Synthesis Path-Upstream   1~30

  • 1
  • [ 1722-12-9 ]
  • [ 14080-23-0 ]
YieldReaction ConditionsOperation in experiment
71% With 3-quinuclidinol In dimethyl sulfoxide at 70℃; for 2.5 h; General procedure: A mixture of 2-chloropyrimidines(10 mmol), potassium cyanide (13–15 mmol), water (20 mmol), and DMSO(20 mL) was heated to 60 C. A solution of 3-quinuclidinol (0.1–0.2 mmol) inDMSO(5 mL) was added to the reaction mixture over 0.5 h. The reaction mixturewas stirred at 50–70 C for additional hours as specified in Table 1. Uponcompletion, the mixture was cooled to room temperature and water (50 mL) wasadded. The resulting mixture was extracted with isopropyl acetate (3 40 mL)(product 7a precipitated out after water addition and was collected by filtration).The combined organic layers were washed with water (2 30 mL), dried overMgSO4, filtered, and concentrated under vacuum to give crude 2-cyanopyrimidines, which were purified by column chromatography (SiO2) to afford pureproducts.
65% With 1,4-diaza-bicyclo[2.2.2]octane In water; dimethyl sulfoxide at 20℃; for 48 h; Synthesis of Pyrimidine-2-carbonitrile [0504] To a stirred solution of 2-chloropyrimidine (20.0 g, 174.6 mmol) in DMSO (40 mL) were added DABCO (3.72 g, 33.17 mmol), KCN (12.48 g, 192 mmol) and drop-wise addition of H20 (15 mL) at RT. The resulting solution was stirred at RT for 48 h. After consumption of starting material by TLC, the reaction mixture was diluted with water and extracted with EtO Ac. Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was triturated with Hexane to afford pyrimidine-2-carbonitrile (12 g, 65percent) as dark brown solid. 1H-NMR (DMSO-d6, 400 MHz): δ 9.04 (s, 2H), 8.92 (d, 1H); LC-MS: 99.41percent; 107.6 (M+2); (column; X-bridge C-18, (50x3.0 mm, 3.5μ); RT 1.14 min. 0.1percent Aq TFA: ACN; 0.8 ml/min); TLC: 30percent EtOAc/Hexane (Rf: 0.2)
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 36, p. 5055 - 5057
[2] Patent: WO2013/142269, 2013, A1, . Location in patent: Paragraph 0503
[3] Patent: WO2012/40230, 2012, A1, . Location in patent: Page/Page column 79-80
  • 2
  • [ 1722-12-9 ]
  • [ 557-21-1 ]
  • [ 14080-23-0 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 9, p. 1711 - 1714
  • 3
  • [ 1722-12-9 ]
  • [ 151-50-8 ]
  • [ 14080-23-0 ]
Reference: [1] Chemical Communications, 2006, # 3, p. 341 - 343
[2] Organic Preparations and Procedures International, 1994, vol. 26, # 6, p. 684 - 687
  • 4
  • [ 1722-12-9 ]
  • [ 14080-23-0 ]
Reference: [1] Pharmaceutical Bulletin, 1955, vol. 3, p. 175,176
[2] Annales de Chimie (Cachan, France), 1960, vol. <13>5, p. 351,399,402
[3] Patent: US5883254, 1999, A,
[4] Patent: US5883254, 1999, A,
  • 5
  • [ 773837-37-9 ]
  • [ 4595-60-2 ]
  • [ 14080-23-0 ]
Reference: [1] Patent: US2003/229079, 2003, A1, . Location in patent: Page 40
  • 6
  • [ 39232-40-1 ]
  • [ 14080-23-0 ]
Reference: [1] Synthetic Communications, 2000, vol. 30, # 8, p. 1509 - 1514
  • 7
  • [ 13435-20-6 ]
  • [ 14395-12-1 ]
  • [ 14080-23-0 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 2007, vol. 72, # 8, p. 1094 - 1106
[2] Liebigs Annalen der Chemie, 1981, # 2, p. 333 - 341
  • 8
  • [ 10442-39-4 ]
  • [ 14080-23-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1437 - 1441
  • 9
  • [ 1722-12-9 ]
  • [ 143-33-9 ]
  • [ 14080-23-0 ]
Reference: [1] Chimia, 1996, vol. 50, # 11, p. 538 - 543
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 26, p. 4420 - 4425
[3] Chimia, 1996, vol. 50, # 11, p. 538 - 543
  • 10
  • [ 1722-12-9 ]
  • [ 773837-37-9 ]
  • [ 14080-23-0 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2676 - 2699
  • 11
  • [ 151-50-8 ]
  • [ 14395-12-1 ]
  • [ 14080-23-0 ]
Reference: [1] Chimia, 1996, vol. 50, # 11, p. 538 - 543
  • 12
  • [ 1722-12-9 ]
  • [ 75-50-3 ]
  • [ 14080-23-0 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 905
  • 13
  • [ 17043-94-6 ]
  • [ 7677-24-9 ]
  • [ 14080-23-0 ]
  • [ 42839-04-3 ]
Reference: [1] Synthesis, 1984, # 8, p. 681 - 683
  • 14
  • [ 88511-48-2 ]
  • [ 14080-23-0 ]
Reference: [1] Annales de Chimie (Cachan, France), 1960, vol. <13>5, p. 351,399,402
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 248, p. 250
  • 15
  • [ 38275-60-4 ]
  • [ 14080-23-0 ]
Reference: [1] Annales de Chimie (Cachan, France), 1960, vol. <13>5, p. 351,399,402
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 248, p. 250
  • 16
  • [ 89581-38-4 ]
  • [ 14080-23-0 ]
Reference: [1] Annales de Chimie (Cachan, France), 1960, vol. <13>5, p. 351,399,402
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 248, p. 250
  • 17
  • [ 14080-23-0 ]
  • [ 31519-62-7 ]
YieldReaction ConditionsOperation in experiment
35.4%
Stage #1: With potassium hydroxide In water for 3 h; Reflux
Stage #2: With hydrogenchloride In water at 20℃;
Pyrimidine-2-carboxylic acid (11):To a stirred solution of pyrimidine-2-carbonitrile (10) (201 mg, 1.914 mmol) in water (5 mL), KOH (214.3 mg, 3.83 mmol) was added and the reaction was refluxed for 3 h. After consumption of the starting material (by TLC), the reaction was slowly brought to RT, neutralized with 2N HC1 and water was removed from the reaction mixture to give the crude residue which was extracted with EtOAc. The combined organic extracts were filtered through a pad of celite and the filtrate was concentrated under reduced pressure to provide compound 11 (84 mg, 35.4percent) which was carried for the next step without any purification.TLC: 80percent EtOAc/Hexane (Rf: 0.05)1H NMR (400MHz, CD3OD-d4): δ 8.83 (br s, 2H), 7.47 (t, J = 4.8 Hz, 1H).
0.10 g at 70℃; for 0.5 h; To the flask was added 0.10g of 2cyanopyrimidine,12percent by mass aqueous sodium hydroxide solution 13mL was stirred at 70 30 minutes. Of 1N dilutehydrochloric acid to pH ~ 3 by adding little by little and, by concentration of the resulting organic layer was extracted three times with 10mL of ethyl acetate, to give0.10g of Compound A218
Reference: [1] Dalton Transactions, 2011, vol. 40, # 20, p. 5476 - 5482
[2] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2676 - 2699
[3] Chemical Communications, 2016, vol. 52, # 54, p. 8459 - 8462
[4] Patent: WO2013/13238, 2013, A2, . Location in patent: Page/Page column 49
[5] Patent: KR2015/128789, 2015, A, . Location in patent: Paragraph 0818; 0820; 0821
[6] Inorganic Chemistry, 2018, vol. 57, # 11, p. 6266 - 6282
  • 18
  • [ 14080-23-0 ]
  • [ 67-56-1 ]
  • [ 34253-03-7 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: at 0℃; for 0.5 h;
Stage #2: at 20 - 50℃; for 19 h;
Step A:
Preparation of methylpyrimidine-2-carboxylate:
HCl gas was bubbled through methanol ("MeOH", 700 mL) at a temperature of 0° C. for 30 minutes to give a saturated solution. Pyrimidine-2-carbonitrile (21.585 g, 205.38 mmol) was added to this solution, and the mixture was stirred at room temperature for 16 hours and then at a temperature ranging from about 40 to about 50° C. for 3 hours.
The reaction mixture was concentrated, and the residue was dissolved in water.
The pH was adjusted to about 7.0 using solid NaHCO3.
The aqueous layer was extracted with 20percent isopropyl alcohol ("iPrOH")/dichloromethane ("DCM") (3*).
The combined organics were dried over sodium sulfate, filtered and concentrated under vacuum to give the desired product as white solids (23.0 g, 81percent).
1H NMR (400 MHz, CDCl3) δ 8.97-8.96 (d, J=4.7 Hz, 2H), 7.53-7.50 (t, J=4.7 Hz, 1H), 4.09 (s, 3H).
81%
Stage #1: at 0 - 50℃;
Stage #2: With sodium hydrogencarbonate In water
Step A: Methyl pyrimidine-2-carboxylate: HCl gas was bubbled through 700 ml MeOH as 0° C. to give a saturated solution. Pyrimidine-2-carbonitrile (21.585 g, 205.38 mmol)was added and the reaction was stirred at ambient temperature for 16 hours at, then heated at 40-50° C. for 3 hours. The solvent was evaporated under vacuum, leaving an off-white semi-solid, which was dissolved water and the pH adjusted 7.0 using NaHCO3. The mixture was extracted with 20percent iPrOH/CH2Cl2, dried over sodium sulfate and concentrated under vacuum to white residue (23.0 g, 81percent).Step A: Preparation of methylpyrimidine-2-carboxlate: To a cold (0° C.) solution of saturated HCl in MeOH (60 mL) was added a solution of pyrimidine-2-carbonitrile (1.4 g, 13 mmol) in MeOH (10 mL). The reaction mixture was stirred at room temperature overnight. Methanol was removed and the resulting white solids were triturated with ether (200 mL). The solids were dissolved in water (20 mL) and the pH was adjusted to 4 with saturated NaHCO3 The aqueous layer was extracted with CH2Cl2 (3.x.100 mL). The combined organics were dried, filtered and concentrated to give a white solid (0.8 g), which was used in the next step without purification.
65%
Stage #1: at 0 - 55℃; for 14.1667 h;
[00119] Preparation 3, Step 1: A solution of 2-cyanopyrimidine, (26 g, 24.8 mmol) in anhydrous MeOH (150 mL) was placed in a 250 ml pressure bottle and cooled to 0 0C. Anhydrous HCl was bubbled through the solution for 10 min. The reaction vessel was capped and heated at 55 0C for 14 h. The mixture was cooled and concentrated in vacuo. The resultant residue was treated with CHCI3 / isopropyl <n="56"/>alcohol (3: 1, 150 mL) and washed with saturated NaHCψ3 and brine. The organic phase was dried (Na2SO4) and concentrated to give methyl pyrimidine-2-carboxylate (2.1 g, 65 percent).
65%
Stage #1: at 0 - 55℃; for 14.1667 h;
[00119] Preparation 3, Step 1: A solution of 2-cyanopyrimidine, (26 g, 24.8 mmol) in anhydrous MeOH (150 mL) was placed in a 250 ml pressure bottle and cooled to 0 0C. Anhydrous HCl was bubbled through the solution for 10 min. The reaction vessel was capped and heated at 55 0C for 14 h. The mixture was cooled and concentrated in vacuo. The resultant residue was treated with CHCI3 / isopropyl <n="56"/>alcohol (3: 1, 150 mL) and washed with saturated NaHCψ3 and brine. The organic phase was dried (Na2SO4) and concentrated to give methyl pyrimidine-2-carboxylate (2.1 g, 65 percent).
32.5% for 16 h; Reflux Methyl pyrimidine-2-carboxylate (11):A stirred solution of cyano 10 (1.01 g, 9.52 mmol) in methanolic HC1 (20 mL, 4N solution) was refluxed for 16 h and concentrated under reduced pressure; the residue was diluted with water and neutralized with sodium bicarbonate solution. The aqueous layer was extracted with 20percent IPA/CH2CI2, dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to afford ester 11 (0.43 g, 32.5percent) as liquid.TLC: 100percent EtOAc (Rf: 0.1)1H NMR (500MHz, CDC13): δ 8.96 (d, J = 5.0 Hz, 2H), 7.50 (t, J = 5.0 Hz, 1H), 4.08 (s, 3H). Mass (ESI): 139 (M++l).

Reference: [1] Patent: US2010/63066, 2010, A1, . Location in patent: Page/Page column 15
[2] Patent: US2007/49603, 2007, A1, . Location in patent: Page/Page column 78; 53
[3] European Journal of Organic Chemistry, 2005, # 15, p. 3297 - 3303
[4] Patent: WO2008/42925, 2008, A1, . Location in patent: Page/Page column 54-55
[5] Patent: WO2008/42925, 2008, A1, . Location in patent: Page/Page column 54-55
[6] Patent: WO2013/13238, 2013, A2, . Location in patent: Page/Page column 33
[7] Patent: US2003/229079, 2003, A1, . Location in patent: Page 40
[8] Patent: US2007/49603, 2007, A1, . Location in patent: Page/Page column 53
[9] Patent: WO2012/40230, 2012, A1, . Location in patent: Page/Page column 80
[10] Patent: WO2013/142269, 2013, A1, . Location in patent: Paragraph 0505; 0506
  • 19
  • [ 14080-23-0 ]
  • [ 34253-03-7 ]
YieldReaction ConditionsOperation in experiment
58% With HCl(g) In methanol; water Preparation of pyrimidine-2-carboxylic Acid Methyl Ester:
To a saturated HCl(g)/MeOH solution (40 mL) was added a solution of 2-cyanopyrimidine (1.97 g, 18.7 mmol) in MeOH (6 mL) at 0° C.
The solution was stirred at room temperature for 30 minutes then poured into diethyl ether (200 mL) to give a colourless precipitate that was collected by filtration.
The crude material was dissolved in H2O (50 mL), adjusted to pH 4 using saturated NaHCO3(aq) and 10percent HCl(aq) then extracted with CHCl3 (5*25 mL).
The combined organic extracts were washed with saturated NaHCO3(aq) (25 mL) then dried (MgSO4) and concentrated in vacuo to give a colourless solid (1.49 g, 58percent).
1H NMR (CDCl3) δ 4.08 (s, 3H), 7.51 (t, 1H, J=5.1 Hz), 8.96 (d, 2H, J=5.1 Hz).
Reference: [1] Patent: US2004/19058, 2004, A1,
  • 20
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  • [ 42839-08-7 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2676 - 2699
[2] Inorganic Chemistry, 2018, vol. 57, # 11, p. 6266 - 6282
  • 21
  • [ 14080-23-0 ]
  • [ 75-16-1 ]
  • [ 53342-27-1 ]
YieldReaction ConditionsOperation in experiment
74.6%
Stage #1: at -5 - 0℃;
Stage #2: With hydrogenchloride; water; ammonium chloride In tetrahydrofuran; diethyl ether at 20℃; for 0.666667 h;
Stage #3: With potassium carbonate In tetrahydrofuran; diethyl ether; water at 0℃;
l-(pyrimidin-2-yl)ethenone may be prepared as follows:A solution of pyrimidine-2-carbonitrile (75 g, 713.62 mmol) in THF (750 ml, 10 vol) was added dropwise to a solution of Methylmagnesium bromide (3.0M in diethylether) (357 ml, 1070.44 mmol) in THF (750 ml) at -5°C. The resulting yellow suspension/solution was stirred at O0C overnight, and added to a rapidly stirred mixture of saturated ammonium chloride solution (750 ml) and 4M HCl (450 ml) at 5°C, then pH adjusted to 1 with additional 2M HCl (5mL). The solution was warmed to 2O0C, stirred for 40 minutes, cooled to 00C then pH adjusted to 6.5-7 by addition of saturated K2CO3 solution (37.5 ml), warmed to 1O0C and separated. The aqueous phase was further extracted into ethyl acetate (5 x 750 ml). Sodium chloride was added to saturate the aqueous phase, which was extracted further into ethyl acetate (750 ml). The pH of the aqueous phase was adjusted to 7-8 by addition of saturated K2CO3 solution, and extracted further with ethyl acetate (3 x 750 ml). The combined organics were washed with saturated brine (750 ml), dried over MgSO4, filtered and concentrated in vacuo to give 78.9g of a brown solid. The crude product was purified by flash silica chromatography, elution in EtOAc. Pure fractions were evaporated to dryness to afford 1- (pyrimidin-2-yl)ethanone (65.Og, 74.6 percent) as a yellow crystalline solid. 1H NMR (400.132 MHz, DMSO) δ 2.67 (3H, s), 7.72 (IH, t), 9.02 (2H, d); m/z (M+H)+, 123.
48% at -5 - 0℃; A solution of 2-cyano-pyrimidine (10.0 g, 95.2 mmol) in THF (100 mL) was cooled to -5 °C and treated with a 3 M solution of methyl magnesium bromide in THF (38.0 mL, 98.4 mmol). The reaction was stirred at 0 °C for two hours until completion was observed by TLC (chloroform/methanol, 9:1 ). The reaction mixture was poured in water; the pH was adjusted to 5-6 and the aqueous layer was extracted with ethyl acetate (3 x 150 mL). The combined organic layers were concentrated under reduced pressure and the crude compound was purified by column chromatography, eluting with chloroform to afford the target compound (6.5 g, 48percent).HPLC purity: 97.2percent (223 nm).Mass spectroscopy: (ESI +ve) 123.1 [M+H]+
Reference: [1] Patent: WO2008/117051, 2008, A1, . Location in patent: Page/Page column 37
[2] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 4, p. 1041 - 1046
[3] Patent: WO2011/95625, 2011, A1, . Location in patent: Page/Page column 95
[4] Chemical Communications, 2017, vol. 53, # 88, p. 12016 - 12019
  • 22
  • [ 14080-23-0 ]
  • [ 917-64-6 ]
  • [ 53342-27-1 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1999, vol. 64, # 7, p. 1159 - 1179
[2] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1981, vol. 17, # 7, p. 710 - 714[3] Khimiya Geterotsiklicheskikh Soedinenii, 1981, # 7, p. 958 - 962
  • 23
  • [ 14080-23-0 ]
  • [ 54198-88-8 ]
Reference: [1] Patent: WO2012/40230, 2012, A1,
[2] Patent: WO2013/142269, 2013, A1,
  • 24
  • [ 14080-23-0 ]
  • [ 75985-45-4 ]
YieldReaction ConditionsOperation in experiment
95% With palladium 10% on activated carbon; hydrogen In ethanol for 12 h; Inert atmosphere Pyrimidin-2-ylmethanamine (24):To a stirred solution of pyrimidine-2-carbonitrile (10) (0.2 g, 0.9 mmol) in EtOH (1 mL), 10percent Pd/C (20 mg) was added under N2 atmosphere. The reaction mixture was stirred under H2 at atmospheric pressure (balloon) for 12 h and filtered through a celite pad. The filtrate was concentrated under reduced pressure to give the crude material which was passed through neutral alumina (EtOAc/Hexane 1 : 1) to afford compound 24 (0.19 g, 95percent).TLC: 50percent EtOAc/Hexane (Rf: 0.1)1H NMR (400MHz, CDC13): δ 8.70 (d, J = 5.2 Hz, 2H), 7.16 (t, J = 4.8 Hz, 1H), 4.19 (s, 1H), 4.11-4.08 (m, 1H).
44% With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol; water at 20℃; for 3 h; To a stirring solution of 2-cyanopyrimidine (2.0 g, 19.0 mmol) in methanol (50 mL) were added 10percentPd/C (300 mg), 12 N HCI (1.5 mL) under 2 atmosphere. The reaction mixture was stirred under atmosphere (balloon pressure) at RT for 3 h. After consumption of the starting material (by TLC), the reaction mixture was filtered through a pad of celite and the pad was washed with methanol. Obtained filtrate was concentrated under reduced pressure to afford crude compound which was triturated with diethyl ether to obtained compound 2S-Y (1.2 g, 44percent) as white solid. 1H-NMR: (500 MHz, DMSO-i): δ 8.87 (d, J= 5.0 Hz, 2H), 8.69 (br s, 2H), 7.52 (t, J= 5.0 Hz, 1H), 4.24 (s, 2H); Mass (ESI): 1 10.3 [M++l]
Reference: [1] Patent: WO2013/13238, 2013, A2, . Location in patent: Page/Page column 42
[2] Patent: WO2014/120783, 2014, A1, . Location in patent: Paragraph 00143
[3] Patent: US5312823, 1994, A,
  • 25
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  • [ 150726-89-9 ]
  • [ 150728-12-4 ]
Reference: [1] Patent: US2012/136015, 2012, A1, . Location in patent: Page/Page column 6-7
  • 26
  • [ 14080-23-0 ]
  • [ 150728-12-4 ]
Reference: [1] Organic Preparations and Procedures International, 2016, vol. 48, # 6, p. 481 - 491
  • 27
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  • [ 150728-13-5 ]
Reference: [1] Patent: WO2011/24056, 2011, A2,
[2] Patent: US2012/136015, 2012, A1,
[3] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 658 - 670
[4] Organic Preparations and Procedures International, 2016, vol. 48, # 6, p. 481 - 491
  • 28
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  • [ 150727-06-3 ]
Reference: [1] Patent: WO2011/24056, 2011, A2,
[2] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 658 - 670
[3] Organic Preparations and Procedures International, 2016, vol. 48, # 6, p. 481 - 491
  • 29
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  • [ 42839-09-8 ]
Reference: [1] Patent: WO2012/40230, 2012, A1,
[2] Patent: WO2013/13238, 2013, A2,
[3] Patent: WO2013/142269, 2013, A1,
  • 30
  • [ 14080-23-0 ]
  • [ 631-61-8 ]
  • [ 312613-82-4 ]
Reference: [1] Crystal Growth and Design, 2018, vol. 18, # 4, p. 2210 - 2216
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5-Chloropyrimidine-2-carbonitrile

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Chemical Structure| 38275-55-7

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5-Fluoropyrimidine-2-carbonitrile

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Chemical Structure| 37972-24-0

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2-Ethynylpyrimidine

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Pyrimidin-2-ylmethanamine

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