Home Cart 0 Sign in  
X

[ CAS No. 10320-42-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
3d Animation Molecule Structure of 10320-42-0
Chemical Structure| 10320-42-0
Chemical Structure| 10320-42-0
Structure of 10320-42-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 10320-42-0 ]

Related Doc. of [ 10320-42-0 ]

Alternatived Products of [ 10320-42-0 ]

Product Details of [ 10320-42-0 ]

CAS No. :10320-42-0 MDL No. :MFCD04117995
Formula : C4H2ClN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :OFCBNMYNAHUDGE-UHFFFAOYSA-N
M.W : 159.53 Pubchem ID :82544
Synonyms :

Calculated chemistry of [ 10320-42-0 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 35.86
TPSA : 71.6 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) : -6.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.94
Log Po/w (XLOGP3) : 0.99
Log Po/w (WLOGP) : 1.04
Log Po/w (MLOGP) : -0.94
Log Po/w (SILICOS-IT) : -0.41
Consensus Log Po/w : 0.32

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.83
Solubility : 2.36 mg/ml ; 0.0148 mol/l
Class : Very soluble
Log S (Ali) : -2.08
Solubility : 1.32 mg/ml ; 0.00828 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.64
Solubility : 3.67 mg/ml ; 0.023 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93

Safety of [ 10320-42-0 ]

Signal Word:Danger Class:9
Precautionary Statements:P261-P264-P270-P271-P272-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338+P310-P333+P313-P403+P233-P405-P501 UN#:3335
Hazard Statements:H302-H315-H317-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 10320-42-0 ]

* 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 [ 10320-42-0 ]
  • Downstream synthetic route of [ 10320-42-0 ]

[ 10320-42-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 10320-42-0 ]
  • [ 56621-90-0 ]
YieldReaction ConditionsOperation in experiment
98% for 6 h; Reflux 4.2.6. Synthesis of 2-chloropyrimidin-5-amine (8). A mixture of 2-chloro-5-nitropyrimidine (0.160 g, 1 mmol), iron powder (0.200 g,3.6 mmol), dried ethanol (2.5 mL), and acetic acid (0.4 mL) wasrefluxed for 6 h, which was then diluted with ethyl acetate, andneutralized with aqueous NaHCO3 before it was filtered with Celite.The filtrate was extracted with ethyl acetate (20 mL3), washedwith brine, and dried over MgSO4. Evaporation of the solvents givesa yellow solid of 8. Yield: 0.127 g, 98percent. 1H NMR (600 MHz, DMSOd6):8.03 (s, 2H), 5.76 (br s, 2H). 13C NMR (150 MHz, DMSO-d6):146.0, 144.2, 142.3. FTIR (KBr, cm1): 3394, 3332, 3212, 1649, 1585,1545, 1412, 1163, 644. MS (EI, m/z): calcd: 129.0; found: 129 (M).
98% at 75℃; for 2 h; To a solution of 36 (400 mg, 2.5 mmol) in HOAc (5 mL) is added Fe (700 mg.12.5 mmoi). After stirring at 75 °C for 2 hours, the mixture is cooled to room temperature, filtered, concentrated, and purified by silica gel column chromatography (F:A:PE == 1:5) to give 37 as as an oil (320 mg. 98percent yield). (MS: [M+Hj 1300)
85% With iron; acetic acid In ethanol; water at 70℃; Example 7
Synthesis of 5-amino-2-chloropyrimidine
Compound 40
Referring to the reaction scheme of , to 140 g (0.88 mol) of 2-chloro-5-nitropyrimidine (39) dissolved in 700 mL of EtOH was added a mixture of 1400 mL of acetic acid, 700 mL water and 197 g of iron powder (70 m mesh, <212 μm).
The mixture was heated overnight at 70° C. and then cooled to r.t. and then filtered.
EtOH was removed from the filtrate in vacuo, and the pH was adjusted to 8 with 12 N NaOH and the product was extracted overnight with continuous liquid-liquid extraction with EtOAc.
The resulting filter cake was washed with EtOAc, and the combined EtOAc layers were washed with water, then brine, dried over magnesium sulfate, and filtered.
After removal of the solvent in vacuo and recrystallization with EtOH, 97.2 g (85percent) of pale brown solid product 39 was obtained. 1H NMR (DMSO-d6) δ 8.94 (s, 2H), 5.77 (brs, 2H).
60%
Stage #1: With iron; acetic acid In ethanol; water at 80 - 90℃; for 1 h;
Stage #2: With ammonia In ethanol; water at 20℃;
Example 41Synthesis of N-(2-chloro-5-pyrimidinyl)-4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-amineThe compound was synthesized according to Method A.A suspension of 3.5 g (63 mmol) of iron dust in 10 mL of 1.5percent aq. AcOH and 35 mL of 65percent EtOH was heated to 80° C., and 1.005 g (6.28 mmol) of 2-chloro-5-nitropyrimidine was added. The reaction mixture was then heated at 90° C. for 1 hr. After cooling to room temperature, the reaction mixture was neutralized with aq. NH3, filtered through celite, and concentrated in vacuo. The residue was extracted with EtOAc (.x.4), and the organic layer was washed with brine, dried (Na2SO4), and concentrated. Chromatography on silica, eluting with hexanes/EtOAc (6:4), gave 0.49 g (60percent yield) of 5-amino-2-chloropyrimidine as a yellow powder: 1H NMR (DMSO-d6) δ8.03 (s, 2H); LCMS (APCI+) m/z: 130 (MH+, 100percent).A mixture of 0.28 g (0.71 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole, 0.076 g (0.56 mmol) of the above amine, 0.026 g (0.04 mmol) of BINAP, 0.01 g (0.04 mmol) of Pd(OAc)2, and 0.266 g (0.82 mmol) of Cs2CO3 in 1,4-dioxane (4 mL) was heated at 100° C. for 3 hrs under nitrogen. The mixture was cooled to room temperature, sat. NaHCO3 solution was added, and the resulting mixture was extracted with EtOAc (.x.4). The organic layer was washed with brine, dried (Na2SO4), and concentrated. Chromatography on silica, eluting with CH2Cl2/EtOAc (6:1), gave 0.10 g (36percent yield) of N-(2-chloro-5-pyrimidinyl)-4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-amine, as a white powder: mp 295° C. (decomp.); 1H NMR (DMSO-d6) δ10.43 (s, 1H), 9.08 (s, 2H), 8.09-7.69 (m, 2H), 7.42 (t, J=8.0 Hz, 1H), 6.98 (d, J=7.6 Hz, 1H), 3.98 (s, 3H), 3.83 (s, 4H), 3.75-3.73 (m, 4H); Anal. Calcd. for C20H18ClF2N9O2: C, 49.0; H, 3.7; N, 25.7. Found: C, 49.2; H, 3.9; N, 25.45percent.
58% With acetic acid In methanol for 3 h; Acetic acid (15 mL, 261 mmol, 8 equiv) was slowly added to a stirred mixture of iron powder (11 g, 196 mmol, 6 equiv), 2-chloro-5-nitro-pyrimidine (5.3 g, 3 3. 33 m mol, 1 e quiv), a nd m ethanol (75 mL). Note: the reaction will exotherm if the acetic acid is added rapidly. After three hours, the reaction mixture was diluted with EtOAc (300 mL), filtered through celite, and neutralized with aqueous K2CO3 (200 mL). The organic layer was separated, washed with H20 (200 mL) and brine (200 mL), dried (NA2SO4), filtered, and concentrated to give 2 as a yellow solid (2.5 g, 58percent, m/z+ = 130. 1).
46.4%
Stage #1: With iron; acetic acid In methanol for 3 h;
Stage #2: With potassium carbonate In methanol; water; ethyl acetate
[0091] Acetic acid (15 mL, 261 mmol, 8 equivalents) is slowly dripped into a mixture containing iron powder (11 g, 196mmol, 6 equivalents) and 2-chloro-5-nitro-pyrimidine (5.3 g, 33.33 mmol, 1 equivalent) and methanol (75 mL). After 3hours, the reaction mixture is diluted with ethyl acetate (300 mL) and filtrated through celite. The organic phase is washedsuccessively with saturated aqueous potassium carbonate solution (200 mL) and brine (200 mL), dried through anhydroussodium sulfate, and concentrated to give compound (1-2) (2.0 g, 46.4percent) as a yellow solid.
46.4% With iron; acetic acid In methanol for 3 h; [0099] Acetic acid (15 ml., 261 mmol, 8 equivalents) is slowly dripped into a mixture containing iron powder (11 g, 196 mmol, 6 equivalents) and 2-chloro-5-nitro-pyrimidine (5.3 g, 33.33 mmol, 1 equivalent) and methanol (75 mL). After 3 hours, the reaction mixture is diluted with ethyl acetate (300 mL) and filtrated through celite. The organic phase is washed successively with saturated aqueous potassium carbonate solution (200 mL) and brine (200 mL), dried through anhydrous sodium sulfate, and concentrated to give compound (1-2) (2.0 g, 46.4percent) as a yellow solid
38% With iron; acetic acid In ethanol; water; ethyl acetate Preparation of 2-chloro-pyrimidin-5-ylamine
Iron (3.38 g, 60 mmol) was added to a boiling solution of 2-chloro-5-nitropyrimidine (2.4 g, 15 mmol) in ethanol (40 mL), H2O (20 mL) and acetic acid (5 mL).
The mixture was heated at reflux for a further 20 min then cooled to rt and neutralized with saturated aqueous sodium bicarbonate. EtOAc (100 mL) was added and the mixture was filtered through a pad of celite.
The filtrate was washed with H2O (50 mL) and brine (20 mL).
The organic layer was dried (Na2SO4) and concentrated under reduced pressure.
Column chromatography of the crude material (hexanes/EtOAc: 1:1 to 1:2) gave the desired product as a yellow solid (0.74 g, 38percent).
24.63% With ammonium chloride; zinc In methanol at 0 - 25℃; for 16 h; To a solution of 2-chloro-5-nitropyrimidine (5 g 31.3 mmol) and zinc (20.49 g 313 mmol) in Methanol (150 mL) was added ammonium chloride (16.77 g 313 mmol) at 0 . The resulting mixture was stirred at 25 for 16 hr. After LCMS analysis showed the starting material disappeared the mixture was filtered. The filtrate was concentrated to give the crude product which was purified by column chromatography (PE/EA3/1 to 1/1) . All fractions found to contain product by TLC (PE/EA1/1 Rf0.5) were combined and concentrated to yield a yellow solid of 2-chloropyrimidin-5-amine (1 g 7.72 mmol 24.63 yield) 1HNMR(400 MHz METHANOL-d4) δ 8.04 (s 2H) ES-LCMS m/z 130.1 (M+H) .

Reference: [1] Tetrahedron, 2014, vol. 70, # 35, p. 5730 - 5738
[2] Patent: WO2017/176812, 2017, A1, . Location in patent: Paragraph 0267
[3] Patent: US2014/235858, 2014, A1, . Location in patent: Paragraph 0093
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 22, p. 8796 - 8805
[5] Patent: US2011/9405, 2011, A1, . Location in patent: Page/Page column 56
[6] Patent: WO2005/5382, 2005, A2, . Location in patent: Page 56; 57
[7] Patent: EP2615092, 2013, A1, . Location in patent: Paragraph 0091
[8] Patent: US2013/178470, 2013, A1, . Location in patent: Paragraph 0098
[9] Patent: US2003/181465, 2003, A1,
[10] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 6, p. 481 - 484
[11] Patent: WO2016/37578, 2016, A1, . Location in patent: Page/Page column 96; 97
[12] Journal of the American Chemical Society, 1942, vol. 64, p. 567,569,570
[13] Journal of Medicinal Chemistry, 2010, vol. 53, # 3, p. 1117 - 1127
[14] Patent: WO2010/111483, 2010, A1, . Location in patent: Page/Page column 98
  • 2
  • [ 10320-42-0 ]
  • [ 3073-77-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5112 - 5128
  • 3
  • [ 540-80-7 ]
  • [ 3073-77-6 ]
  • [ 7447-39-4 ]
  • [ 10320-42-0 ]
YieldReaction ConditionsOperation in experiment
50% With magnesium sulfate In diethyl ether; acetonitrile EXAMPLE 1
Preparation of 2-chloro-5-nitro-pyrimidine
5-Nitro-pyrimidin-2-ylamine (A) (0.98 g, 7 mmol, 1 eq) was added to a stirring mixture of anhydrous copper (II) chloride (1.12 g, 8.4 mmol, 1.2 eq), tert-butylnitrite (1.24 mL, 10.5 mmol, 1.5 eq) and MgSO4 (~300 mg) in acetonitrile (40 mL) at 65-80° C. (bath temperature).
After 30 min the mixture was cooled to rt and diethyl ether (100 mL) was added.
The organic layer was separated and washed sequentially with 1N aqueous HCl (2*20 mL), H2O (50 mL) and brine (20 mL).
The organic layer was dried (Na2SO4) and concentrated under reduced pressure.
Column chromatography of the crude material (hexanes/diethyl ether: 3:1) gave the desired product as a pale yellow solid (0.56 g, 50percent).
Reference: [1] Patent: US2003/181465, 2003, A1,
  • 4
  • [ 3264-10-6 ]
  • [ 10320-42-0 ]
YieldReaction ConditionsOperation in experiment
54% for 2 h; Heating / reflux A mixture of 2-hydroxy-5-nitropyrimidine (1.Og, 7.1mmol) and N,N-dimethylaniline (0.9mL, 7.1mmol) in POCl3 (1OmL) was refiuxed for 2h, then was poured onto crushed ice (~100g) and stirred for Ih. The mixture was extracted with DCM (3 x 10OmL), the combined organic layers were dried (MgSO4). Filtration and evaporation of the solvent afforded the product (615mg, 54percent). 1HNMR (CDCl3) 9.39 (2H, s).
Reference: [1] Heterocycles, 1984, vol. 22, # 1, p. 79 - 84
[2] Patent: WO2007/135350, 2007, A1, . Location in patent: Page/Page column 78
  • 5
  • [ 3073-77-6 ]
  • [ 10320-42-0 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 6, p. 481 - 484
  • 6
  • [ 3264-10-6 ]
  • [ 10320-42-0 ]
Reference: [1] Journal of the American Chemical Society, 1942, vol. 64, p. 567,569,570
  • 7
  • [ 10320-42-0 ]
  • [ 124-41-4 ]
  • [ 14001-69-5 ]
YieldReaction ConditionsOperation in experiment
75% for 1 h; Reflux Example 40Synthesis of 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(2-methoxy-5-pyrimidinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amineThe compound was synthesized according to Method A.To a solution of sodium methoxide (0.090 g of sodium) in MeOH (12 mL) was added 0.486 g (3.03 mmol) of 2-chloro-5-nitropyrimidine, and the mixture was heated under reflux for 1 hr. After cooling, the mixture was concentrated in vacuo, extracted with EtOAc, and washed with water. The aqueous layer was extracted with CHCl3 and the combined organic layers were dried (Na2SO4), and concentrated, to give 0.347 g (75percent yield) of 2-methoxy-5-nitropyrimidine as a yellow powder: 1H NMR (CDCl3) δ9.31 (s, 2H), 4.17 (s, 3H); LCMS (APCI+) m/z: 156 (MH+, 100percent).To 0.342 g (2.20 mmol) of the above nitro compound in MeOH (20 mL) was added 0.30 g of 10percent Pd/C and the mixture was stirred under hydrogen (25 in/Hg) for 18 hrs. The reaction mixture was filtered through celite, and concentrated, to give 0.274 g (100percent yield) of 5-amino-2-methoxypyrimidine as a colorless oil: 1H NMR (DMSO-d6) δ 8.05 (s, 2H), 3.94 (s, 3H); LCMS (APCI+) m/z: 126 (MH+, 100percent).To 0.274 g (2.19 mmol) of the above amino compound in THF (3 mL) was added 1.25 mL of NaHMDS (2 M solution in THF) and the mixture was stirred for 10 min. A solution of 0.31 g (0.78 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole in THF (5 mL) was added and the resulting mixture was stirred for 90 min. The reaction mixture was neutralized with acetic acid, diluted with water, and extracted with EtOAc. The organic layer was washed with water and aq. NH3, dried, and concentrated. Recrystallization from EtOH/CH2Cl2 gave 0.098 g (26percent yield) of 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(2-methoxy-5-pyrimidinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine: mp 255-258° C.; 1H NMR (DMSO-d6) 810.07 (s, 1H), 8.88-8.74 (m, 2H), 8.15-7.42 (m, 3H), 6.97 (d, J=8.0 Hz, 1H), 3.98 (s, 3H), 3.93 (s, 3H), 3.82-3.72 (m, 8H); Anal. Calcd. for C21H21F2N6O3: C, 52.0; H, 4.4; N, 26.0. Found: C, 52.1; H, 4.5; N, 26.0percent.
Reference: [1] Patent: US2011/9405, 2011, A1, . Location in patent: Page/Page column 55-56
[2] Journal of the American Chemical Society, 1942, vol. 64, p. 567,569,570
[3] Australian Journal of Chemistry, 1966, vol. 19, p. 2321,2326
[4] Patent: WO2005/3100, 2005, A2, . Location in patent: Page 135
  • 8
  • [ 10320-42-0 ]
  • [ 5188-07-8 ]
  • [ 14001-70-8 ]
YieldReaction ConditionsOperation in experiment
99% at 0 - 20℃; Inert atmosphere A solution of 5 g (31.3 mmol) of 2-chloro-5-nitropyrimidine in 50 mL of THF was cooled to O0C under nitrogen. 2.26 g (32.3 mmol) of sodium thiomethoxide was added. The reaction <n="59"/>was stirred at room temperature for 24 hours. The reaction was monitored by LCMS indicating formation of desired product. The mixture was diluted with 250 mL of diethyl ether and a solid precipitated. The solid was removed by filtration and rinsed with dichloromethane. The filtrate was concentrated in vacuo to afford 5.3 g (99percent) of 2-methylsulfanyl-5-nitropyrimidine.
Reference: [1] Patent: WO2009/149139, 2009, A1, . Location in patent: Page/Page column 56-57
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 10320-42-0 ]

Chlorides

Chemical Structure| 49845-33-2

[ 49845-33-2 ]

2,4-Dichloro-5-nitropyrimidine

Similarity: 0.81

Chemical Structure| 13162-26-0

[ 13162-26-0 ]

2,4-Dichloro-6-methyl-5-nitropyrimidine

Similarity: 0.74

Chemical Structure| 890094-38-9

[ 890094-38-9 ]

2-Chloro-N-isopropyl-5-nitropyrimidin-4-amine

Similarity: 0.74

Chemical Structure| 56621-90-0

[ 56621-90-0 ]

5-Amino-2-chloropyrimidine

Similarity: 0.74

Chemical Structure| 1445894-94-9

[ 1445894-94-9 ]

2-Chloro-4-isopropoxy-5-nitropyrimidine

Similarity: 0.71

Nitroes

Chemical Structure| 49845-33-2

[ 49845-33-2 ]

2,4-Dichloro-5-nitropyrimidine

Similarity: 0.81

Chemical Structure| 3073-77-6

[ 3073-77-6 ]

2-Amino-5-nitropyrimidine

Similarity: 0.75

Chemical Structure| 13162-26-0

[ 13162-26-0 ]

2,4-Dichloro-6-methyl-5-nitropyrimidine

Similarity: 0.74

Chemical Structure| 890094-38-9

[ 890094-38-9 ]

2-Chloro-N-isopropyl-5-nitropyrimidin-4-amine

Similarity: 0.74

Chemical Structure| 1210824-80-8

[ 1210824-80-8 ]

2-Bromo-5-nitropyrimidine

Similarity: 0.72

Related Parent Nucleus of
[ 10320-42-0 ]

Pyrimidines

Chemical Structure| 49845-33-2

[ 49845-33-2 ]

2,4-Dichloro-5-nitropyrimidine

Similarity: 0.81

Chemical Structure| 3073-77-6

[ 3073-77-6 ]

2-Amino-5-nitropyrimidine

Similarity: 0.75

Chemical Structure| 13162-26-0

[ 13162-26-0 ]

2,4-Dichloro-6-methyl-5-nitropyrimidine

Similarity: 0.74

Chemical Structure| 890094-38-9

[ 890094-38-9 ]

2-Chloro-N-isopropyl-5-nitropyrimidin-4-amine

Similarity: 0.74

Chemical Structure| 56621-90-0

[ 56621-90-0 ]

5-Amino-2-chloropyrimidine

Similarity: 0.74