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Chemical Structure| 13036-57-2
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Product Details of [ 13036-57-2 ]

CAS No. :13036-57-2 MDL No. :MFCD00054434
Formula : C5H5ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :BHAKRVSCGILCEW-UHFFFAOYSA-N
M.W : 128.56 Pubchem ID :11629607
Synonyms :

Calculated chemistry of [ 13036-57-2 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
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 : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 1.56
Log Po/w (WLOGP) : 1.44
Log Po/w (MLOGP) : 0.54
Log Po/w (SILICOS-IT) : 2.04
Consensus Log Po/w : 1.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.17
Solubility : 0.859 mg/ml ; 0.00669 mol/l
Class : Soluble
Log S (Ali) : -1.71
Solubility : 2.5 mg/ml ; 0.0194 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.62
Solubility : 0.311 mg/ml ; 0.00242 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.42

Safety of [ 13036-57-2 ]

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 [ 13036-57-2 ]

* 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 [ 13036-57-2 ]
  • Downstream synthetic route of [ 13036-57-2 ]

[ 13036-57-2 ] Synthesis Path-Upstream   1~33

  • 1
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Reference: [1] Yakugaku Zasshi, 1953, vol. 73, p. 643[2] Chem.Abstr., 1954, p. 9364
[3] Yakugaku Zasshi, 1953, vol. 73, p. 643[4] Chem.Abstr., 1954, p. 9364
  • 2
  • [ 13036-57-2 ]
  • [ 75-24-1 ]
  • [ 14331-54-5 ]
Reference: [1] Acta Chemica Scandinavica, 1997, vol. 51, # 3, p. 302 - 306
  • 3
  • [ 5424-21-5 ]
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YieldReaction ConditionsOperation in experiment
74.4% for 2 h; Reflux To the reaction flask were sequentially added 2,4-dichloro-6-methyl-pyrimidine (15.00 g, 92.00 mmol), zinc powder (18.05 g, 276.00 mmol), ammonia (38.70 g, 276 mmol) and stirred at to the reaction flask was added water (120 ml). The reaction was heated at reflux for 2 hours, the reaction solution was cooled to room temperature, suction filtered, the filtrate was extracted with ethyl acetate (2x200 ml), the organic layer was post-saturated brine (150 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure the residue was purified by column chromatography (eluent to PE: EA = 5: 1), to give a white solid 8.8 g, yield 74.4percent
53% With iodine; zinc In ethanol; water at 70℃; for 4 h; Step A: 2-Chloro-4-methylpyrimidine; CH,Q To a vigorously stirred slurry containing 50.0 g (0.31 mol) of 2,6-dichloro-4- methylpyrimidine, 250 ml_ of EtOH and 250 mL of water was added 41 g (0.63 mol) of zinc dust, followed by 0.78 g (3.08 mmol) of iodine. The reaction mixture was heated at 700C for 4 h, then cooled and filtered. The EtOH was removed under reduced pressure and the mixture was extracted with DCM. The combined organic layers were dried over MgSO4, filtered, and the solvent was removed under reduced pressure. The residue was subjected to silica gel chromatography, eluting with a hexane/DCM mixture, to afford 20.6 g (53percent) of the title compound of Step A as a white solid: 1H-NMR (d6-DMSO, 400 MHz) δ 8.59 (d, 1 H, J = 4.9 Hz), 7.44 (d, 1 H, J = 4.9 Hz), and 3.29 (s, 3 H); ESIMS: 129.11 (M+H+).Step A: 2-Chloro-4-methylpyrimidineCH,Q To a vigorously stirred slurry containing 50.0 g (0.31 mol) of 2,6-dichloro-4- methylpyrimidine, 250 ml_ of EtOH and 250 mL of water was added 41 g (0.63 mol) of zinc dust, followed by 0.78 g (3.08 mmol) of iodine. The reaction mixture was heated at 700C for 4 h, then cooled and filtered. The EtOH was removed under reduced pressure and the mixture was extracted with DCM. The combined organic layers were dried over MgSO4, filtered, and the solvent was removed under reduced pressure. The residue was subjected to silica gel chromatography, eluting with a hexane/DCM mixture, to afford 20.6 g (53percent) of the title compound of Step A as a white solid: 1H-NMR (d6-DMSO, 400 MHz) δ 8.59 (d, 1 H, J = 4.9 Hz), 7.44 (d, 1 H, J = 4.9 Hz), and 3.29 (s, 3 H); ESIMS: 129.11 (M+H+).
Reference: [1] Patent: CN105732587, 2016, A, . Location in patent: Paragraph 0117; 0118; 0119
[2] Patent: WO2009/76140, 2009, A1, . Location in patent: Page/Page column 110
[3] Yakugaku Zasshi, 1950, vol. 70, p. 137[4] Chem.Abstr., 1950, p. 5886
[5] Journal of the Chemical Society, 1951, p. 1004,1015[6] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, vol. 24, p. 84
[7] Patent: WO2005/68452, 2005, A1, . Location in patent: Page/Page column 37-38
[8] Patent: WO2004/5282, 2004, A1, . Location in patent: Page 36-38
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YieldReaction ConditionsOperation in experiment
50% at 0℃; for 8 h; Example 1.1.26: (4-methylpyrimidin-2-yl)methanamine; MeMgCl (3M solution in THF, 4.47 mL, 13.42 mmol) was added dropwise to a stirred solution of the 2,4-dichloropyrimidine (2 g, 13.42 mmol) and Fe(acac)3 (1.37 g, 3.9 mmol) in THF (40 mL) under argon at 0 0C and the resulting reaction mixture was stirred at 0 0C for 8 h. The reaction mixture was diluted with water and extracted with EtOAc. Evaporation of the organic phase followed by column chromatography on a silica gel (eluting with 25percent EtOAc/hexanes) to afford 2-chloro-4-methylpyrimidine in 50percent yield.
Reference: [1] Patent: WO2009/42694, 2009, A1, . Location in patent: Page/Page column 83
  • 5
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Reference: [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 9, p. 5515 - 5522
[2] Asian Journal of Chemistry, 2014, vol. 26, # 21, p. 7397 - 7400
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2016, vol. 191, # 1, p. 48 - 54
[4] Phosphorus, Sulfur and Silicon and the Related Elements, 2017, vol. 192, # 1, p. 34 - 41
[5] Chinese Journal of Chemistry, 2015, vol. 33, # 10, p. 1124 - 1134
[6] Letters in Drug Design and Discovery, 2016, vol. 13, # 4, p. 343 - 351
[7] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 167 - 178
[8] Journal of Fluorine Chemistry, 2016, vol. 184, p. 36 - 44
  • 6
  • [ 1722-12-9 ]
  • [ 917-54-4 ]
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YieldReaction ConditionsOperation in experiment
67%
Stage #1: at -30 - 0℃; for 1 h;
Stage #2: With water; acetic acid In tetrahydrofuran; diethyl ether at 0℃; for 0.166667 h;
Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; diethyl ether at 20℃; for 0.5 h;
To a finely dispersed suspension of 2-chloropyrimidine (8.01 g, 69.9 mmol) in a 10: 1 mixture of [ET2O-THF] (500 mL) [AT-30°C] was added dropwise MeLi (46 mL, 1.6M in [ET20,] 73.6 mmol). The reaction mixture was stirred [AT-30°C] for 30 min, and was then warmed to [0°C] and stirred for 30 min. To the reaction mixture was then added a 1: 1: 20 mixture of H2O- [HOAC-THF] (100 mL), and the mixture was stirred at [0°C] for 10 min. To the mixture was then added a solution of DDQ (16.7 g, 73.6 mmol) in THF (100 [ML),] and the mixture was stirred and warmed to room temperature for 30 min. The mixture was then diluted with [ET2O] (300 mL) and washed with IN aq. [NAOH] [(3X100] [ML)] followed by brine (300 mL). The organic phase was then dried over anhydrous [MGSO4,] filtered, concentrated in vacuo, and purified by flash chromatography using EtOAc-hexanes (1: 2) as eluent to afford 6.06 g of 2-chloro-4- methylpyrimidine (67percent) as white crystalline plates. To a solution of 2-chloro-4-methylpyrimidine (6.06 g, 47.1 mmol) in [MEOH] (40 [ML)] was added hydrazine monohydrate (10 mL, 206 [MMOL).] The solution was stirred for 16 h at room temperature and then purified by reverse phase HPLC to provide 4.43 g of the title compound [(76percent)] as a white solid. MH+ 125.
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 17, p. 4137 - 4140
[2] Patent: WO2003/101442, 2003, A1, . Location in patent: Page 53
[3] Patent: US6342503, 2002, B1, . Location in patent: Example 8
  • 7
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YieldReaction ConditionsOperation in experiment
69% for 6 h; Heating / reflux 2-Chloro-4-methyl-pyrimidine (51):
To a stirred mixture of 4-Methyl-pyrimidin-2-ol (29.3 g, 0.2 mol) in phosphorus(III) oxychloride (200 ml) was added N,N-diethylaniline (31.8 ml, 0.2 mol).
The mixture was refluxed for 6 hr.
After cooling to room temperature, the mixture was evaporated in vacuo and ether was added to the residue.
The ether layer was taken, washed with 2N aqueous sodium hydroxide solution, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo.
The residue was purified by silica gel column chromatography (eluent, ether:hexane (1:1)) to afford 18 g (69percent) of a white solid. 1H NMR (200 MHz, CDCl3) δ: 2.55 (3H, s), 7.14 (1H, d, J=4.6 Hz), 8.47 (1H, d, J=4.6 Hz).
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 10, p. 1653 - 1656
[2] Patent: US2008/70920, 2008, A1, . Location in patent: Page/Page column 41-42
  • 8
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  • [ 75-16-1 ]
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Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 11, p. 3943 - 3949
  • 9
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  • [ 75-24-1 ]
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Reference: [1] Patent: US2003/229079, 2003, A1, . Location in patent: Page 40-41
  • 10
  • [ 1722-12-9 ]
  • [ 84-58-2 ]
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Reference: [1] Patent: US6107301, 2000, A,
  • 11
  • [ 3934-20-1 ]
  • [ 75-24-1 ]
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Reference: [1] Acta Chemica Scandinavica, 1997, vol. 51, # 3, p. 302 - 306
  • 12
  • [ 1134-81-2 ]
  • [ 288-13-1 ]
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  • [ 4472-44-0 ]
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
  • 13
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
  • 14
  • [ 5348-51-6 ]
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Reference: [1] Bulletin des Societes Chimiques Belges, 1957, vol. 66, p. 276,289
[2] Journal of the Chemical Society, 1951, p. 1004,1015[3] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, vol. 24, p. 84
  • 15
  • [ 15018-56-1 ]
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Reference: [1] Yakugaku Zasshi, 1950, vol. 70, p. 137[2] Chem.Abstr., 1950, p. 5886
  • 16
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Reference: [1] Yakugaku Zasshi, 1950, vol. 70, p. 137[2] Chem.Abstr., 1950, p. 5886
  • 17
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Reference: [1] Yakugaku Zasshi, 1950, vol. 70, p. 137[2] Chem.Abstr., 1950, p. 5886
  • 18
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Reference: [1] Yakugaku Zasshi, 1950, vol. 70, p. 137[2] Chem.Abstr., 1950, p. 5886
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
  • 20
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
  • 24
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
  • 26
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  • [ 4637-24-5 ]
  • [ 14001-60-6 ]
  • [ 99357-40-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1996, vol. 33, # 2, p. 465 - 474
  • 27
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  • [ 124-41-4 ]
  • [ 14001-60-6 ]
Reference: [1] Yakugaku Zasshi, 1942, vol. 62, p. 315,333; dtsch. Ref. S. 95, 106[2] Chem.Abstr., 1951, p. 5150
[3] Journal of the Chemical Society, 1951, p. 1004,1015[4] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, vol. 24, p. 84
  • 28
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Reference: [1] Yakugaku Zasshi, 1951, vol. 71, p. 1420[2] Chem.Abstr., 1952, p. 8095
[3] Yakugaku Zasshi, 1951, vol. 71, p. 1420[4] Chem.Abstr., 1952, p. 8095
  • 29
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  • [ 63-74-1 ]
  • [ 127-79-7 ]
Reference: [1] Yakugaku Zasshi, 1950, vol. 70, p. 283,284[2] Chem.Abstr., 1951, p. 2894
  • 30
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  • [ 59215-36-0 ]
YieldReaction ConditionsOperation in experiment
81% With potassium carbonate In water at 50 - 60℃; for 1 h; General procedure: By reacting the diazonium salts of 4,6-disubstituted pyrimidin-2-amines with concentrated HCl and ZnCl2,24 2-chloro-4,6-disubstituted pyrimidines 2 were prepared. Referring to the literature,23 compounds 3 were prepared and the method wasimproved. To a stirred solution of piperazine (45 mmol) andK2CO3 (16.5 mmol) in water (20 mL) was added chloropyrimidine2 (18 mmol) in small portions at 50–60C. The mixturewas stirred for 1 h at 60–65C and cooled to room temperature.The yellow solid, 1,4-bis(4,6-disubstituted pyrimidin-2-yl)piperazine, was filtered off, and the filtrate was then extractedthree times with chloroform, dried over Na2SO4, evaporated invacuum to give 3, which was used for the following reactionswithout further purification.3a: yellow solid, yield 81percent, mp 45–48C; 3b: yellow solid,yield 79percent, mp 82–84C.
81% With potassium carbonate In water at 35 - 65℃; General procedure: 2-Chloro-4,6-disubstituted-pyrimidines 17 were prepared bythe reaction of the diazoniumsalts of 4,6-disubstituted-pyrimidin-2-amines (16) with concentrated hydrochloric acid and ZnCl2 [35].Compound 18 was prepared according to literature [32], and themethod was improved. To a stirred solution of piperazine(45 mmol) and K2CO3 (16.5 mmol) in water (20 mL) was addedchloropyrimidine 17 (18 mmol) in small portions at 50e65 C. Themixture was stirred for 1 h at 60e65 C and cooled to 35 C. Theyellowsolid, 1,4-bispyrimidylpiperazine byproduct, was filtered off,and the filtrate was then extracted three times with chloroform,dried over Na2SO4, and evaporated in vacuum to give compound 18,which was used for the following reactions without further purification.
81% With potassium carbonate In water at 50 - 65℃; General procedure: 2-Chloro-4,6-disubstituted pyrimidines (II) were prepared by reaction of the diazonium salts of 4,6-disubstituted pyrimidin-2-amines with concentrated hydrochloric acid and ZnCl2 [43]. Compounds (III) were prepared according to the known protocol [42] and the method was improved. To a stirred solution of piperazine (45 mmol) and K2CO3 (16.5 mmol) in water (20 mL), chloropyrimidine (II) (18 mmol) was added in small portions at 50- 65 °C. The mixture was stirred for 1 h at 60-65 °C and cooled to 35 °C. The yellow solid (1,4-disubstituted piperazine byproduct), was filtered off, and the filtrate was extracted three times with chloroform, dried over Na2SO4, and concentrated to give (III), which were used in the subsequent step without further purification. (IIIa): yellow solid, yield 81percent, mp 45-48 °C; (IIIb): yellow solid, yield 79percent, mp 82-84 °C.
Reference: [1] Chinese Journal of Chemistry, 2015, vol. 33, # 10, p. 1124 - 1134
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2016, vol. 191, # 1, p. 48 - 54
[3] Letters in Drug Design and Discovery, 2016, vol. 13, # 4, p. 343 - 351
[4] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 167 - 178
[5] Journal of Fluorine Chemistry, 2016, vol. 184, p. 36 - 44
[6] Journal of Chemical Research, 2006, # 12, p. 809 - 811
[7] Phosphorus, Sulfur and Silicon and the Related Elements, 2017, vol. 192, # 1, p. 34 - 41
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Reference: [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 9, p. 5515 - 5522
  • 32
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  • [ 130645-48-6 ]
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 10, p. 1653 - 1656
  • 33
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  • [ 149849-92-3 ]
Reference: [1] Patent: CN106083734, 2016, A, . Location in patent: Paragraph 0016; 0019; 0020; 0021; 0022; 0024; 0025
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