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[ CAS No. 75833-38-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 75833-38-4
Chemical Structure| 75833-38-4
Chemical Structure| 75833-38-4
Structure of 75833-38-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 75833-38-4 ]

CAS No. :75833-38-4 MDL No. :MFCD00234989
Formula : C5H2ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :HXVQPZSXXYOZMP-UHFFFAOYSA-N
M.W : 139.54 Pubchem ID :246647
Synonyms :

Calculated chemistry of [ 75833-38-4 ]

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 : 31.76
TPSA : 49.57 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) : -6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.25
Log Po/w (XLOGP3) : 1.22
Log Po/w (WLOGP) : 1.0
Log Po/w (MLOGP) : -0.43
Log Po/w (SILICOS-IT) : 1.54
Consensus Log Po/w : 0.92

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.97
Solubility : 1.51 mg/ml ; 0.0108 mol/l
Class : Very soluble
Log S (Ali) : -1.86
Solubility : 1.93 mg/ml ; 0.0139 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.33
Solubility : 0.657 mg/ml ; 0.00471 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 75833-38-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 75833-38-4 ]

* 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 [ 75833-38-4 ]
  • Downstream synthetic route of [ 75833-38-4 ]

[ 75833-38-4 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 7460-56-2 ]
  • [ 75833-38-4 ]
YieldReaction ConditionsOperation in experiment
86.5%
Stage #1: at 0 - 20℃; for 0.5 h;
Stage #2: for 0.5 h; Reflux
Step 7) A mixture of 2-oxo-l,2-dihydro-pyrimidi7ne-4-carbaldehyde oxime 10 (72.6 g) in cold (0 °C) phosphorus oxychloride (280 ml) was warmed slowly with vigorous stirring until a vigorous reaction commenced, at which time warming was discontinued. Once complete dissolution had taken place, N,N-diethylaniline (36.3 mL) was added and the reaction mixture was refluxed for another 30 minutes. After cooling to room temperature, the POCl3 was removed under reduced pressure and the the crude was taken up with ice-water (500 mL). The mixture was extracted with DCM (5 x 200 mL). The combined organics was dried over Na2S04 and concentrated. The residue was filtered through short silica gel column (washed with DCM). After concentration, the product 11 (63 g, solidified upon standing, 86.5percent) was used in the next step directly.
Reference: [1] Patent: WO2013/39854, 2013, A1, . Location in patent: Page/Page column 39
[2] Patent: WO2005/75468, 2005, A2, . Location in patent: Page/Page column 43
  • 2
  • [ 7460-56-2 ]
  • [ 75833-38-4 ]
YieldReaction ConditionsOperation in experiment
60% for 4 h; Step 2) Preparation of 2-chloro pyrimidine-4-carbonitrile; The compound obtained in Step 1 (4 g, 28.7 mmol) was added to 10 mi of trichlorophosphrous, and the mixture was stirred for 4 hours. The resulting mixture was concentrated under a reduced pressure to remove the solvent, and sequentially washed with sodium bicarbonate solution (200 ml*2) and salt solution. The resulting residue was subjected to silica gel column <n="51"/>chromatography (eluent: n-hexane/ethyl acetate=4:l) to obtain the title compound (2.4 g; yield: 60 percent).
30% at 45 - 70℃; for 3 h; Prepared largely according to the method described in WO2005/075468. A solution of 4-methyl-lH-pyrimidin-2-one hydrochloride (14.7g, lOOmmol) in 50percent aqueous acetic acid (100ml) at 15°C was treated with sodium nitrite in one portion (10.4g, 150mmol) with vigorous stirring causing an exothermic reaction (40°C). A yellow precipitate was filtered off, washed with cold water and dried in a vacuum dessicator to afford the 2- hydroxy-pyrimidine-4-carbaldehyde oxime intermediate as a pale yellow solid (13. lg, 94percent) JH NMR (400 MHz, DMSO-d6) δ 12.44 (s, 1H), 11.87 (br s, 1H), 7.92 (d, J = 6.3 Hz, 1H), 7.77 (d, J = 0.4 Hz, 1H), 6.66 (dd, J = 6.4, 0.9 Hz, 1H). The oxime was treated with phosphorus oxychloride (20ml) and warmed slowly to 45°C. Warming was stopped as the temperature rose suddenly to 70°C and the mixture stirred for 3h. Diisopropylethylamine (2ml) was added and the mixture refluxed for 30mins before pouring into ice and extraction with DCM. The organics were washed with water then NaHC03 (sat aqu) then again with water, dried (MgS04), filtered and evaporated to afford Intermediate lid as a yellow oil which crystallized on standing (1.51g, 30percent). JH NMR (400 MHz, DMSO-d6) δ 9.15 (d, J = 4.9 Hz, 1H), 8.25 (d, J = 4.9 Hz, 1H).
30% at 45 - 70℃; for 3 h; [0110] A solution of 4-methyl-1H-pyrimidin-2-one hydrochloride (14.7g, 100mmol) in 50percent aqueous acetic acid (100ml)at 15°C was treated with sodium nitrite in one portion (10.4g, 150mmol) with vigorous stirring causing an exothermicreaction (40°C). A yellow precipitate was filtered off, washed with cold water and dried in a vacuum dessicator to afford the 2-hydroxy-pyrimidine-4-carbaldehyde oxime intermediate as a pale yellow solid (13.1g, 94percent) 1H NMR (400 MHz,DMSO-d6) δ 12.44 (s, 1H), 11.87 (br s, 1H), 7.92 (d, J = 6.3 Hz, 1H), 7.77 (d, J = 0.4 Hz, 1H), 6.66 (dd, J = 6.4, 0.9 Hz,1H). The oxime was treated with phosphorus oxychloride (20ml) and warmed slowly to 45°C. Warming was stopped asthe temperature rose suddenly to 70°C and the mixture stirred for 3h. Diisopropylethylamine (2ml) was added and themixture refluxed for 30mins before pouring into ice and extraction with DCM. The organics were washed with water thenNaHCO3 (sat aqu) then again with water, dried (MgSO4), filtered and evaporated to afford Intermediate IVd as a yellowoil which crystallized on standing (1.51g, 30percent). 1H NMR (400 MHz, DMSO-d6) δ 9.15 (d, J = 4.9 Hz, 1H), 8.25 (d, J =4.9 Hz, 1H).
Reference: [1] Patent: WO2007/73117, 2007, A1, . Location in patent: Page/Page column 49-50
[2] Patent: WO2015/144614, 2015, A1, . Location in patent: Page/Page column 37; 38
[3] Patent: EP3144307, 2017, A1, . Location in patent: Paragraph 0110
  • 3
  • [ 557-21-1 ]
  • [ 3934-20-1 ]
  • [ 75833-38-4 ]
Reference: [1] Patent: WO2010/36632, 2010, A1, . Location in patent: Page/Page column 220; 221
  • 4
  • [ 950514-12-2 ]
  • [ 75833-38-4 ]
Reference: [1] Patent: US2002/40025, 2002, A1,
  • 5
  • [ 75833-38-4 ]
  • [ 22536-66-9 ]
Reference: [1] Patent: US2002/40025, 2002, A1,
[2] Patent: US5164397, 1992, A,
[3] Patent: WO2008/57336, 2008, A2, . Location in patent: Page/Page column 44
  • 6
  • [ 75833-38-4 ]
  • [ 5188-07-8 ]
  • [ 1124-75-0 ]
YieldReaction ConditionsOperation in experiment
66% for 2 h; Heating / reflux Reference Example 103
6-Cyano-2-methylthiopyrimidine
A mixture of 2-chloro-6-cyanopyrimidine (2.20 g, 15.8 mmol), sodium thiomethoxide (1.22 g, 17.3 mmol) and THF (100 ml) was refluxed for 2 hrs..
The reaction mixture was combined with ethyl acetate and water..
The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate..
The solvent was evaporated to give the titled compound (1.57 g, 66 percent) as pale yellow crystals.1H-NMR (CDCl3) δ: 2.58 (3H, s), 7.26(1H, d, J = 4.8 Hz), 8.70 (1H, d, J = 4.8 Hz). IR(KBr): 2241, 1554, 1537, 1396, 1348, 1197, 862 cm-1.
Reference: [1] Patent: EP1424336, 2004, A1, . Location in patent: Page 210
  • 7
  • [ 75833-38-4 ]
  • [ 75825-60-4 ]
Reference: [1] Polish Journal of Chemistry, 1980, vol. 54, # 2, p. 335 - 340
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