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[ CAS No. 100859-35-6 ] {[proInfo.proName]}

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Chemical Structure| 100859-35-6
Chemical Structure| 100859-35-6
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Product Details of [ 100859-35-6 ]

CAS No. :100859-35-6 MDL No. :MFCD00234162
Formula : C6H5ClN4 Boiling Point : -
Linear Structure Formula :- InChI Key :KKTMNZXPLHVDBC-UHFFFAOYSA-N
M.W : 168.58 Pubchem ID :5408997
Synonyms :

Calculated chemistry of [ 100859-35-6 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.17
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.66
TPSA : 54.46 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) : -6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.16
Log Po/w (XLOGP3) : 1.46
Log Po/w (WLOGP) : 1.31
Log Po/w (MLOGP) : 0.33
Log Po/w (SILICOS-IT) : 2.17
Consensus Log Po/w : 1.29

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.41
Solubility : 0.655 mg/ml ; 0.00389 mol/l
Class : Soluble
Log S (Ali) : -2.21
Solubility : 1.04 mg/ml ; 0.00617 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.16
Solubility : 0.116 mg/ml ; 0.000687 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.75

Safety of [ 100859-35-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 100859-35-6 ]

* 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.

  • Downstream synthetic route of [ 100859-35-6 ]

[ 100859-35-6 ] Synthesis Path-Downstream   1~45

  • 1
  • [ 5167-18-0 ]
  • [ 100859-35-6 ]
  • 2
  • [ 100859-35-6 ]
  • 2-FC6H4CH2-Cl(or Br) [ No CAS ]
  • [ 1026172-67-7 ]
  • 3
  • [ 100859-35-6 ]
  • [9-(2-Fluoro-benzyl)-2-methyl-9H-purin-6-yl]-methyl-amine [ No CAS ]
  • 4
  • [ 91-59-8 ]
  • [ 100859-35-6 ]
  • [ 1163260-09-0 ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 20℃; [0161] Synthesis of 2-methyl-N-(naphthalen-2-yl)-9H-purin-6-amine.; [0162] This compound is synthesized according the scheme above and is characterized as follows: melting point: 85 0C. 1H NMR (300 MHz, DMSO-d6): d 10.45 (brs, NH, exchangeable), 8.65 (s, IH), 8.57 (s, IH), 7.91-7.99 (m, 4H), 7.46-7.56 (m, 2H), 2.71 (s, 3H); MS m/z : 276.1 (M + H+).
  • 5
  • [ 5167-18-0 ]
  • [ 100859-35-6 ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate; In N,N-dimethyl acetamide; at 140 - 160℃; [0161] Synthesis of 2-methyl-N-(naphthalen-2-yl)-9H-purin-6-amine.; [0162] This compound is synthesized according the scheme above and is characterized as follows: melting point: 85 0C. 1H NMR (300 MHz, DMSO-d6): d 10.45 (brs, NH, exchangeable), 8.65 (s, IH), 8.57 (s, IH), 7.91-7.99 (m, 4H), 7.46-7.56 (m, 2H), 2.71 (s, 3H); MS m/z : 276.1 (M + H+).
  • 6
  • [ 536-90-3 ]
  • [ 100859-35-6 ]
  • [ 1096435-75-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In butan-1-ol; at 110℃; for 3h; Example 16; 2-Methyl-6-(3-methoxyanilino)purineTo a suspension of 2-methyl-6-chloropurine (1.69 g; 0.01 mol) and m-anisidine (1.23 g; 0.01 mol) in n-butanol (20 ml), triethylamine (3.5 ml; 0.025 mol) was added. The resulting thick suspension was stirred at 110 C. for 3 hours, when TLC showed the absence of starting material and the presence of desired product. The reaction mixture was then cooled to room temperature. The white precipitate was filtered off, rinsed with n-butanol (2×10 ml) and water (3×10 ml) and dried into constant weight. Yield: 1.92 g (75%). The crude product was purified as hydrochloride salt by the crystallization from 2.5 M methanolic hydrochloric acid. TLC (chloroform-methanol-NH4OH; 4:1:0.05): one single spot, free of starting material. HPLC purity: 99+%.
  • 7
  • [ 933-80-2 ]
  • [ 122-51-0 ]
  • [ 100859-35-6 ]
YieldReaction ConditionsOperation in experiment
at 100℃; for 1.25h; 6-Chloro-2-methylpyrimidine-4,5-diamine (8.89 g, 56.1 mmol, the material from Step 1) was suspended in ethyl ortho formate (100 mL, 601 mmol) in a flask fitted with a reflux condenser and placed in a preheated oil bath (100 0C) and stirred for 75 minutes. The reaction mixture was cooled to room temperature, concentrated, treated with hexanes and filtered. The solid washed with hexanes and dried to give 6-chloro-2-methyl-9H-purine. MS (ESI pos. ion) m/z: 169. Calcd: 168.
5.3 g at 100℃; for 4h; A mixture of <strong>[933-80-2]6-chloro-2-methyl-pyrimidine-4,5-diamine</strong> (4.8 g, 30.27 mmol, 1 eq) , diethoxymethoxyethane (13.46 g, 90.80 mmol, 15.10 mL, 3 eq), and then the mixture was stirred at 100 C for 4 hr. The reaction mixture was filter and the filter cake was obtained, filtrate was diluted with water 5 mL extracted with EtOAc 15 mL (5 mL * 3). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue, combined with filter cake, compound 6-chloro-2-methyl-9H-purine (I-792) (5.3 g) was obtained as a yellow solid. LCMS m/z 168.8 (M+1)+.
  • 8
  • [ 110-87-2 ]
  • [ 100859-35-6 ]
  • [ 1253568-59-0 ]
YieldReaction ConditionsOperation in experiment
6-Chloro-2-methyl-9H-purine (9.45 g, 56 mmol, the material from Step 2) was suspended in DCM (100 mL) and p-toluenesulfonic acid (Acros Organics, Geel, Belgium, 12% in acetic acid, 0.90 mL, 5.6 mmol) and 2,3-dihydropyran (6.6 mL, 73 mmol) were added. The reaction flask was fitted with a reflux condenser and placed in a preheated oil bath (50 0C) and stirred under nitrogen for 30 minutes. The reaction mixture was cooled to room temperature and stirred overnight. After stirring overnight, the reaction mixture was diluted with DCM and treated with saturated sodium bicarbonate (75 mL). The layers were separated, and the aqueous phase was extracted with DCM. The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and dried under high vacuum at 45 0C (in a water bath) and then at room temperature and then at 60 0C and finally at room temperature again to afford 6-chloro-2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (13.73 g, 97% over 3 steps). MS (ESI pos. ion) m/z: 253. Calcd. MS: 252. 1H NMR (CDCl3, 400 MHz) δ 8.26 (s, IH), 5.78 (d, J = 10.56 Hz, IH), 4.19 (d, J = 11.93 Hz, IH), 3.84 - 3.76 (m, IH), 2.80 (s, 3H), 2.20 - 1.96 (m, 3H), 1.89 - 1.64 (m, 3H).
  • 10
  • [ 100859-35-6 ]
  • [ 1253568-61-4 ]
  • 11
  • [ 100859-35-6 ]
  • [ 1253569-39-9 ]
  • 12
  • [ 100859-35-6 ]
  • [ 1253569-38-8 ]
  • 13
  • [ 100859-35-6 ]
  • [ 1253569-41-3 ]
  • 14
  • [ 100859-35-6 ]
  • [ 1253569-40-2 ]
  • 16
  • [ 91-59-8 ]
  • [ 100859-35-6 ]
  • [ 1163260-10-3 ]
  • 17
  • [ 613-13-8 ]
  • [ 100859-35-6 ]
  • [ 1393709-14-2 ]
  • 18
  • [ 580-17-6 ]
  • [ 100859-35-6 ]
  • [ 1393709-15-3 ]
  • 19
  • [ 16617-46-2 ]
  • [ 100859-35-6 ]
  • [ 1393709-17-5 ]
  • 20
  • [ 580-15-4 ]
  • [ 100859-35-6 ]
  • [ 1393709-16-4 ]
  • 21
  • [ 676-58-4 ]
  • [ 18552-90-4 ]
  • [ 100859-35-6 ]
YieldReaction ConditionsOperation in experiment
91% With Pd-catalysis; In butan-1-ol; at 80℃; for 24h; Example 5 2-methyl-6-chloropurine 3 mmol of 2-Iodo-6-chloropurine was dissolved in 20 mL of butanol and then 4 mmol of MeMgCl was added. The mixture was reacted at 80 C. for 24 hr under Pd-catalysis. After cooling, the product was filter out and washed with water and butanol and crystallized from dimethyformamide or ethanol. HPLC: purity>97%. Yield 91%.
  • 22
  • [ 100859-35-6 ]
  • [ 4152-90-3 ]
  • 2-methyl-6-(3-chlorobenzylamino)purine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In butan-1-ol; at 90℃; for 4h; Example 6 2-methy-6-(3-chlorobenzylamino)purine 3 mmol of 2-methyl-6-chloropurine from example 5 were dissolved in 20 mL of butanol and then 4 mmol of 3-chlorobenzylamine and 6 mmol of triethylamine were added. The mixture was reacted at 90 C. for 4 hr. After cooling, the product was filter out and washed with water and butanol and crystallized from dimethyformamide or ethanol. HPLC: purity>98%. Yield 93%. Table 4 compound prepared by the method of example 6
  • 23
  • [ 933-80-2 ]
  • [ 149-73-5 ]
  • [ 100859-35-6 ]
YieldReaction ConditionsOperation in experiment
50% Reflux; Step 2: A solution of <strong>[933-80-2]6-chloro-2-methylpyrimidine-4,5-diamine</strong> (474 mg, 3.0 mmol ) in trimethoxymethane (15 mL) was heated to reflux overnight. The reaction mixture was concentrated and water was added, extracted with EtOAc. The organic layer was separated and washed with water and brine, dried over a2S04 and concentrated. Purification by a flash column chromatography (0-30% EtOAc in petroleum ether) gave 6-chloro-2-methyl-9H- purine (250 mg, 50% yield). LC-MS: m/z 169 (M+H)+.
  • 24
  • [ 100859-35-6 ]
  • N-(1-(3-fluoro-4-(trifluoromethyl)phenyl)cyclopropyl)-2,9-dimethyl-9H-purin-6-amine [ No CAS ]
  • 25
  • (R)-1-(3-fluoro-4-(trifluoromethyl)phenyl)-2,2-dimethylpropan-1-amine hydrochloride [ No CAS ]
  • [ 100859-35-6 ]
  • C18H19F4N5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 120℃; for 24h;Inert atmosphere; To a microwave tube charged with a stir bar was added <strong>[100859-35-6]6-chloro-2-methyl-9H-purine</strong> (0.15 g, 0.89 mmol) [CAS 100859-35-61 followed by (R)- 1 -(3-fluoro-4-(trifluoromethyl)phenyl)-2,2- dimethylpropan-1-amine hydrochloride (0.38 g, 1.34 mmol). NMP (3 mL) was added followed by dropwise addition of DIEA (0.47 mL, 2.7 mmol). The tube was purged to N2, capped, and was heated to 120 C. The mixture was stirred at 120 C for 24 h, cooled to RT, and the mixture wasdiluted with EtOAc (50 mL). The organic layer was washed with water (2x) and brine (lx). The organic layer was dried over Na2504, filtered, and concentrated under reduced pressure. The residue was purified by reverse phase HPLC chromatography (SureFire C18, 20-90% ACN in water (0.05% TFA)) to afford the title compound as a solid. ‘H NMR (CDC13, 500 MHz) ö: 8.74 (br s, 1H), 8.37(br s, 1H), 7.59 (s, 1H), 7.36 (m, 2H), 5.45 (d, J = 9.0 Hz, 1H), 2.73 (s, 3H), 1.18 (s, 9H).LC/MS (m/z): 382.1 (M+H).
  • 26
  • [ 100859-35-6 ]
  • [ 74-88-4 ]
  • [ 40423-36-7 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 12h;Inert atmosphere; To a solution of <strong>[100859-35-6]6-chloro-2-methyl-9H-purine</strong> (500 mg, 2.97 mmol) in DMF (12 mL) under N2 at RT was added K2C03 (1.64 g, 11.86 mmol) followed by dropwise addition of iodomethane (0.30 mL,4.75 mmol). The mixture was stirred at RT for 12 h whereupon it was diluted with EtOAc (100 mL). The organic layer was washed with water (2 x 30 mL) and brine (30 mL). The organic layer was dried over Na2504, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (15-30% EtOAc in hexanes) to afford the title compound as a solid. LC/MS (m/z): 183.1 (M+H).
  • 27
  • [ 52162-55-7 ]
  • [ 100859-35-6 ]
  • 2-methyl-6-chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranos-1-yl)purine [ No CAS ]
  • 28
  • [ 100859-35-6 ]
  • 2-methyl-6-sulfhydryl-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythropentofuranos-1-yl)purine [ No CAS ]
  • 29
  • [ 100859-35-6 ]
  • 2-methyl-6-sulfhydryl-9-(2-deoxy-β-D-erythro-pentofuranos-1-yl)purine [ No CAS ]
  • 30
  • [ 100859-35-6 ]
  • 2-methyl-6-cyanoethylthio-9-(2-deoxy-β-D-erythro-pentofuranos-1-yl)purine [ No CAS ]
  • 31
  • [ 100859-35-6 ]
  • 2-methyl-6-cyanoethylthio-9-(2-deoxy-5-O-dimethoxytrityl-β-D-erythro-pentofuranos-1-yl)purine [ No CAS ]
  • 32
  • [ 100859-35-6 ]
  • C44H52N7O6PS [ No CAS ]
  • 33
  • [ 100859-35-6 ]
  • [ 934-23-6 ]
  • 34
  • [ 100859-35-6 ]
  • 9-(2-deoxy-3,5-di-O-toluoyl-β-D-ribofuranosyl)-2-methylpurine [ No CAS ]
  • 35
  • [ 100859-35-6 ]
  • 7-(2-deoxy-3,5-di-O-toluoyl-β-D-ribofuranosyl)-2-methylpurine [ No CAS ]
  • 36
  • [ 100859-35-6 ]
  • 9-(2-deoxy-β-D-ribofuranos-1-yl)-2-methylpurine [ No CAS ]
  • 37
  • [ 100859-35-6 ]
  • 7-(2-deoxy-β-D-ribofuranos-1-yl)-2-methylpurine [ No CAS ]
  • 38
  • [ 100859-35-6 ]
  • 9-(2-deoxy-5-O-dimethoxytrityl-β-D-ribofuranos-1-yl)-2-methylpurine [ No CAS ]
  • 39
  • [ 100859-35-6 ]
  • (2-deoxy-5-O-dimethoxytrityl-1-(2-methylpurin-9-yl)-β-D-ribofuranos-3-yl)-(2-cyanoethyl-N,N- diisopropyl) -phosphoramidite [ No CAS ]
  • 40
  • [ 100859-35-6 ]
  • 6-iodo-2-methyl-9H-purine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogen iodide; at 18℃; for 0.2h; A solution of <strong>[100859-35-6]6-chloro-2-methyl-9H-purine</strong> (4.1 g, 24.32 mmol, 1 eq) in HI (15 mL) (purity 47%) the mixture was stirred at 18 C for 0.2 hr. The reaction mixture was filter and filter cake 6-iodo-2-methyl-9H-purine (I-793) (5.3 g) was obtained as a yellow solid. LCMS m/z 260.8 (M+1)+.
  • 41
  • [ 100859-35-6 ]
  • 6-iodo-2-methyl-9-tetrahydropyran-2-yl-purine [ No CAS ]
  • 42
  • [ 100859-35-6 ]
  • (((((2R,3R,4S,5R)-5-(6-(benzylamino)-2-methyl-9H-purin-9-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)methyl)phosphonic acid [ No CAS ]
  • 43
  • [ 100859-35-6 ]
  • C18H20FN5O3 [ No CAS ]
  • 44
  • [ 100859-35-6 ]
  • C32H28FN5O5 [ No CAS ]
  • 45
  • [ 97614-44-3 ]
  • [ 100859-35-6 ]
  • C25H20ClFN4O5 [ No CAS ]
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