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CAS No. : | 1046816-75-4 | MDL No. : | MFCD16659172 |
Formula : | C5H5ClN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OHMILAMAADHENX-UHFFFAOYSA-N |
M.W : | 144.56 | Pubchem ID : | 54150633 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 33.17 |
TPSA : | 46.01 Ų |
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) : | -6.98 cm/s |
Log Po/w (iLOGP) : | 1.4 |
Log Po/w (XLOGP3) : | 0.28 |
Log Po/w (WLOGP) : | 0.47 |
Log Po/w (MLOGP) : | -0.34 |
Log Po/w (SILICOS-IT) : | 1.42 |
Consensus Log Po/w : | 0.65 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.34 |
Solubility : | 6.61 mg/ml ; 0.0457 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.81 |
Solubility : | 22.5 mg/ml ; 0.156 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.08 |
Solubility : | 1.22 mg/ml ; 0.00841 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.43 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a dry flask was added <strong>[287714-35-6]methyl 2-chloropyrimidine-5-carboxylate</strong> (17 mg) and THF (5 mL). The mixture was cooled to -780C and a solution of DIBAL-H in hexane (1 M, 1.2 mL) was added slowly. The resulting mixture was stirred at -780C to it overnight, then quenched with saturated aqueous Na2SO4. The solution was filtered. Solvents were removed under reduced pressure to give (2-chloropyrimidin-5-yl)methanol. MS calcd. for [M+H]+ CsH6ClN2O: 145.1; found: 145.1. | ||
A solution of <strong>[287714-35-6]2-chloropyrimidine-5-carboxylic acid methyl ester</strong> (l .Og, 5.8mmol) in THF (30mL), under argon, was cooled to -78°C. To the solution was added a solution of DIBAL-H in DCM (1.0M, 20.3mL, 20.3mmol), slowly over 40min. The reaction was allowed to warm to r. t. before continuing to stir for a further 16 h. A solution of sat. sodium potassium tartrate (lOOmL) was slowly added, followed by EtOAc, and the mixture was stirred vigorously for 2 h. The organic phase was separated then a further portion of EtOAc was added to the aquoues phase before stirring vigorously for lh. The organic phase was removed and the aqueous phase was washed with a mixture of EtOAc and THF (1 :1). All organic fractions were combined and washed with sat. sodium potassium tartrate solution, water, then brine, and dried (MgS04). The solvent was removed in vacuo to afford the title compound: RT = 1.62 min; mlz (ES+) = 145.0 [M+ H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 160℃; for 0.166667h;microwave irradiation; | To a reaction vessel was added 2- (methylsulfonyl)-6-(3-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)propoxy)- 1,2,3,4-tetrahydroisoquinoline (20 mg), <strong>[1046816-75-4](2-chloropyrimidin-5-yl)methanol</strong> (10 mg), Pd(PPh3)4 (2 mg), dioxane (2 mL) and Na2CO3 (1 M, 1 mL). The mixture was irradiated in a microwave at 16O0C for 10 min. The mixture was cooled to rt, extracted with CHCl3. The extracts were combined, washed with water, dried (MgSO4) and filtered. Solvents were removed under reduced pressure to give crude product. Purification of the crude on silica gel column (EtOAc: Hexanes = 2: 1) afforded the desired product. MS calcd. for [M+H]+ C25H29N2O4S: 453.2; found: 453.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Pd(PPh3)4; In toluene; | [2-(4-Methoxy-2-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol A mixture of <strong>[1046816-75-4](2-Chloro-pyrimidin-5-yl)-methanol</strong> (350 mg, 5.81 mmol), 4-Methoxy-2-trifluoromethyl-phenylboronic acid (700 mg, 1.2 eq.) Pd(PPh3)4 (5 mol percent) in toluene (10 mL) and Na2CO3 (aq. 2N, 4 mL) was sparged with argon and refluxed for 60 minutes. The reaction was cooled, partitioned between EtOAc and water and the organics dried with brine and Na2SO4. The crude product was purified by silica gel chromatography eluding with 80percent EtOAc: hexanes. MS 285 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hydrogenchloride; | (2-Chloro-pyrimidin-5-yl)-methanol A solution of <strong>[120747-85-5](2-Amino-pyrimidin-5-yl)-methanol</strong> (400 mL, 3.2 mmol) was dissolved in HCl (aq. 3M, 20 mL) and treated with NaNO2 (aq. 1N, 20 mL). The reaction was stirred at 0° C. for 18 hours. The mixture was basified with K2CO3 (aq.) then extracted with DCM (3*50 mL). The organics were washed with more K2CO3 (aq.) and the organics concentrated to give the pure product as needles. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | Diisopropyl azodicarboxylate (0.140 mL, 0.71 mmol) was added to a stirred solution of tert-butyl 4-(5-hydroxypyrimidin-2-yl)piperazine-1-carboxylate (0.16 g, 0.57 mmol), and triphenylphosphine (0.225 g, 0.86 mmol) in THF (5 mL) under nitrogen. The resulting solution was stiffed at 20° C. for 30 minutes and then <strong>[1046816-75-4](2-chloropyrimidin-5-yl)methanol</strong> (0.083 g, 0.57 mmol) was added. The resulting solution was stirred at rt for 24 hours under nitrogen. The solvent was evaporated and the residue diluted with EtOAc and brine. A white ppt was filtered off and dried under vacuum. The aqueous layer was extracted with EtOAc (50 mL) and the combined organics were concentrated in vacuo to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 1 to 4percent MeOH in DCM. The crude product was purified by flash silica chromatography, elution gradient 40 to 100percent EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 4-(5-((2-chloropyrimidin-5-yl)methoxy)pyrimidin-2-yl)piperazine-1-carboxylate (0.100 g, 43percent) as a white solid. 1H NMR (400.132 MHz, CDCl3) 1.49 (9H, s), 3.47-3.52 (4H, m), 3.71-3.75 (4H, m), 5.02 (2H, s), 8.14 (2H, s), 8.69 (2H, s). m/z (ES+) (M+H)+=407; HPLC tR=3.18 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 70℃; for 21h; | To a dry solution of <strong>[1046816-75-4](2-chloropyrimidin-5-yl)methanol</strong> (Preparation 74, 253mg, 1.75mmol) and [(3i?,45)-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester (Preparation 48, 574mg, 1.93mmol) in DMSO (1.6mL) was added DBU (262muEpsilon,1.75mmol) and the reaction was heated to 70°C for 21 h. The mixture was diluted with water and extracted with EtOAc (x 2). The organic fractions were combined, washed with sat. NaHC03 solution, then brine, and dried (MgS04). Removal of the solvent in vacuo and purification by column chromatography (DCM:MeOH, 97:3) afforded the title compound: RT = 3.23 min; mlz (ES+) = 407.1 [M+ H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃; for 0.833333h; | To a solution of <strong>[1046816-75-4]2-chloro-5-hydroxymethyl-pyrimidine</strong> (9.0 g, 62 mmol) in 70 ml of anhydrous DMF was added methyl iodide (6 eq. 370 mmol, 23 ml). The mixture was cooled to 0°C, then NaH (2.6 lg, 1.05 eq.) was added in portions over 5 mins. The resulting mixture was stirred 25 min. at 0°C, then 25 min. at rt. The reaction mixture was then cooled in ice bath, and quenched by addition of saturated NH4C1 aq. solution (200 ml ), extracted with ether (150 ml x 3). The combined organic layers were washed by brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by ISCO column (330 g of silica gel) using ethyl acetate in hexane (0-90percent ethyl acetate, 2500 ml, then 1000 ml of ethyl acetate) to give 6.5g (66percent) of the title compound: MS (ESI) mlz 159.2 (M+H); 1H NMR (500 MHz, CDC13) delta 8.60 (s, 2H), 4.48 (s, 2H), 3.45 (s, 3H). |
66% | With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃; for 0.916667h; | To a solution of <strong>[1046816-75-4]2-chloro-5-hydroxymethyl-pyrimidine</strong> (9.0 g, 62 mmol) in 70 ml of anhydrous DMF was added methyl iodide (6 eq. 370 mmol, 23 ml). The mixture was cooled to 0°C, then NaH (2.6 lg, 1.05 eq.) was added in portions over 5 mins. The resulting mixture was stirred 25 min. at 0°C, then 25 min. at rt. The reaction mixture was then cooled in ice bath, and quenched by addition of saturated NH4CI aq. solution (200 ml ), extracted with ether (150 ml x 3). The combined organic layers were washed by brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by ISCO column (330 g of silica gel) using ethyl acetate in hexane (0-90percent ethyl acetate, 2500 ml, then 1000 ml of ethyl acetate) to give 6.5g (66percent) of the title compound: MS (ESI) mlz 159.2 (M+H); NMR (500 MHz, CDC13) delta 8.60 (s, 2H), 4.48 (s, 2H), 3.45 (s, 3H). |
66% | With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃; for 0.833333h; | To a solution of<strong>[1046816-75-4]2-chloro-5-hydroxymethyl-pyrimidine</strong> (9.0 g, 62 mmol) in 70 ml ofanhydrous DMF was added methyl iodide (6 eq. 370 mmol, 23 ml). The mixture was cooled to0°C, then NaH (2.61g, 1.05 eq.) was added in portions over 5 mins. The resulting mixture wasstirred 25 min. at 0°C, then 25 min. at rt. The reaction mixture was then cooled in ice bath, and10 quenched by addition of saturated NH4Cl aq. solution (200 ml ), extracted with ether (150 ml x3). The combined organic layers were washed by brine, dried over Na2S04, filtered andconcentrated in vacuo. The residue was purified by ISCO column (330 g of silica gel) usingethyl acetate in hexane (0-90percent ethyl acetate, 2500 ml, then 1000 ml of ethyl acetate) to give 6.5g(66percent) of the title compound: 1H NMR (500 MHz, CDCh) 8 8.60 (s, 2H), 4.48 (s, 2H), 3.45 (s,15 3H). MS ESI m/z 159.2 (M+H). |
Preparation of 2-chloro-5-methoxymethylpyrimidine 18To a solution of <strong>[1046816-75-4]2-chloro-5-hydroxymethyl-pyrimidine</strong> (9.0 g, 62 mmol) in 70 ml of anhydrous DMF was added methyl iodide (6 eq. 370 mmol, 23 ml). The mixture was cooled to 0°C, then NaH (2.6 lg, 1.05 eq.) was added in portions over 5 mins. The resulting mixture was stirred 25 min. at 0°C, then 25 min. at rt. The reaction mixture was then cooled in ice bath, and quenched by addition of saturated NH4C1 aq. solution (200 ml ), extracted with ether (150 ml x 3). The combined organic layers were washed by brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by IS CO column (330 g of silica gel) using ethyl acetate in hexane (0-90percent ethyl acetate, 2500 ml, then 1000 ml of ethyl acetate) to give 6.5g (66percent) of the title compound: MS (ESI) mlz 159.2 (M+H); 1H NMR (500 MHz, CDC13) delta 8.60 (s, 2H), 4.48 (s, 2H), 3.45 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In water; N,N-dimethyl-formamide; at 120℃; for 1.33333h;Sealed tube; Microwave irradiation; | (2-Chloropyrimidin-5-yl)methanol (0.49g, 3.39 mmol, 1.0 equiv.), {trans-4-[5- (4,4,5,5-Tetramethyl-l ,3,2-dioxaborolan-2-yl)-pyrimidin-2-yloxy]-cyclohexyl}-acetic acid methyl ester (1.275 g, 3.39 mmol, 1 equiv.), Pd(dppf) (0.124 g, 0.169 mmol, 0.05equiv.), and 2 Na2C03 (aq) (5.48 mL, 10.95 mmol, 4 equiv.) were placed in DMF (15 mL) and stirred at room temperature in a sealed microwave reaction vial. The reaction was placed under vacuum for 5 min (until no continuing gas evolution was detected) and then 2 (g) was bubbled into the reaction suspension for 25 min. The reaction suspension was heated at 120°C under microwave conditions for 1 hr 20 min. The reaction was concentrated to a residue which was then dissolved in EtOAc / brine. The EtOAc phase was dried over Na2SC>4, filtered, and concentrated to an oil. Purification with Biotage SP-1 [ FLASH 25 cartridge. Hexanes:EtOAc 0>12percent 2CV; 12> 100percent 10CV; 100percent 5CV ] to afford methyl (tran5-4-[5-(hydroxymethyl)-2,5'-bipyrimidin-2'-yl]oxy}cyclohexyl)acetate. LC-MS (ES, m/z): C 17H20N4O4: 344; Found: 344 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃; for 1.5h;Cooling with ice; | A solution of the <strong>[1046816-75-4](2-chloropyrimidin-5-yl)methanol</strong> (1 g, 6.92 mmol) in anhydrous DMF (6.92 ml) was cooled at ice-bath temperature and iodoethane (2.236 ml, 27.7 mmol) added. The solution was stirred for 10 minutes at 0°C. Sodium hydride (0.304 g, 7.61 mmol) was added and the resulting mixture stirred at 0°C for 0.5 hours and RT for 60 minutes. The mixture was diluted with saturated ammonium chloride (100 mL) and extracted with EtOAc (3 x 50 mL). The organic fractions were combined, washed with brine (100 mL), dried over Na2S04, filtered and the volatiles removed in vac. The mixture was purified on a 50 g Biotage KP-Si02 cartridge using a gradient eluant of 0-100percent EtOAc:Hexanes, to afford the title compound. LC/MS (m/z): 173(M+H)+- |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
119 mg | With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; at 20℃; for 12h;Cooling with ice; | Preparation Example 10 A mixture of <strong>[1046816-75-4](2-chloropyrimidin-5-yl)methanol</strong> (120 mg), 3,5-dimethoxyphenol (186 mg), tributylphosphine (297 muL), and tetrahydrofuran (2.4 mL) was ice cooled, and 1,1'-(azodicarbonyl)dipiperidine (305 mg) was added thereto followed by stirring at room temperature for 12 hours. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 2-chloro-5-[(3,5-dimethoxyphenoxy)methyl]pyrimidine (119 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20℃; for 0.666667h; | CBr4 (2.68 g, 8.07 mmol) in 5 mL of DCM was added to a stirred, cooled (to 0°C) mixture of <strong>[1046816-75-4](2-chloropyrimidin-5-yl)methanol</strong> (1.19 g, 8.23 mmol) and triphenylphosphine(2.116 g, 8.07 mmol) in 35 mL of DCM and the mixture was stirred at 0°C for 10 mm. Then,the reaction mixture was removed from the ice bath and stirred at RT for 30 mm. TLC showedthe reaction was near completion. The reaction mixture was concentrated to 1/2 volume, filtered and concentrated down. The residue was purified by silica gel column chromatography, eluting with EtOAc/isohexane (030percent) to give the desired product. LC-MS [M+H]: 208.93 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 120℃; for 0.333333h;Microwave irradiation; | (2-Chloropyrimidin-5-yl)methanol (500 mg, 3.46 mmol) is suspended in 1-methyl-2- pyrrolidinone (2 mL) and 3-azabicyclo[3.1.0]hexane hydrochloride (414 mg, 3.46 mmol) and potassium carbonate (1 .2 g, 8.65 mmol) are added. The mixture is heated under microwave irradiation at 120 00 for 20 minutes. The mixture is diluted with ethyl acetate, filtered to remove undissolved salts and the solvent removed undervacuum to give the crude intermediate (Yield 635 mg).LC (Method 5): tR = 0.67 mm; Mass spectrum (ES+): mlz = 192 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With manganese(IV) oxide; In dichloromethane; at 40℃; for 4h; | To a solution of 5 (500 mg. 347 mmoi) in DCM is added activatedrnanganese(1V) oxide (1.5 g, 17.4 mmoi) at room temperature. After stirring at 40 C for 4hours. the mixture is filtered and concentrated to give crude 8 as a solid (400 mg, 80%). (MS:[MH-HJ + 143 0) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With 1H-imidazole; In dichloromethane; at 20℃; for 0.5h;Inert atmosphere; | To <strong>[1046816-75-4](2-chloropyrimidin-5-yl)methanol</strong> (946 mg, 6.5 mmol) stirring in DCM (38 mL) at rt was added imidazole (477 mg, 7 mmol) followed by tertbutyl(chloro)dimethylsilane (1 g, 6.9 mmol). The reaction was stirred at rt for30 mins, then diluted with water. The layers were separated and the aqueous layer was extracted with DCM (X3), dried (Na2SO4), and concentrated under reduced pressure. Purification (FCC, Si02, EtOAc/hexanes 0 - 10percent) afforded the title compound as a clear, colorless oil that solidified upon standing (1 .37 g, 81percent). MS (ESI): mass calcd. for C11H19CIN2OSi, 258.1; m/zfound, 259.0[M+H]. |
78% | With dmap; triethylamine; In tetrahydrofuran; at 20℃; for 16h; | To a solution of 5 (288 mg, 2.0 mmol) in THF is added DMAP (244 mg, 2.0 mmol), TEA (0.25 ml,, 2.0 mmol), and TBSCI (600 mg, 4.0 mmol). After stirring at room temperature for 16 hours, the mixture is concentrated and purified by silica gel column chromatography (MeOH:DCM = 1 : 100) to give 6 as a white solid (400 mg, 78percent yield). (MS: GammaMu+Eta 259.1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 90℃; for 4h; | General procedure: To a solution of and halide in the indicated solvent is added boronic acid or ester, carbonate base, and palladium catalyst at room temperature. After stirring at 100 °C overnight, the mixture is cooled and concentrated.Following Procedure B using 5 (150 mg, 1.04 mmol), 4-pyridinylboronic acid (191 mg, 1.56 mmol), sodium carbonate (220 mg, 2.1 mmol), dioxane (5 mL), water (0.5 mL), and Pd(dppf)Cl2 (50 rng, 0.07 mmol ), react at 90 °C for 4 hours and then purify with silica gel column chromatography (EA:PE = 1 :2) to give A3S as a solid (100 mg, 78percent yield). (MS: [M+H]+ 188.1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃; for 3h; | General procedure: To a solution of and halide in the indicated solvent is added boronic acid or ester, carbonate base, and palladium catalyst at room temperature. After stirring at 100 °C overnight, the mixture is cooled and concentrated.Following Procedure B using 5 (200 mg, I .4 mmoi), cyciopropyihoronic acid(356 rng, 4.15 mmol), sodium carbonate (440 rng, 4.15 rnrnoi), dioxane (10 rnL), water (1rnL), and Pd(PPh3)4 (80 rng, 0.07 mrnoi), react at 10() °C for 3 hours and then purify withsilica gel column chromatography (EA:PE 1:10 to 10:1) to give 64 as a white solid (19 mg,9percent yield). (MS: [M+Hj1 151.1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In ethyl acetate; at 0℃; for 48h; | To a cold (0° C.) solution of <strong>[1046816-75-4](2-chloropyrimidin-5-yl)methanol</strong> (710 mg, 4.9 mmol) and triethylamine (1.8 mL, 13 mmol) in EtOAc (20 mL) was added methanesulfonyl chloride (0.60 mL, 7.8 mmol) by dropwise addition. The resulting mixture was allowed to warm to room temperature and stirred for 2 days. The reaction mixture was added to water and the organic phase was separated. The aqueous phase was extracted with EtOAc, and solvent was removed from the combined organic layers in vacuo. The crude residue was purified by flash chromatography (SiO2, 50percent EtOAc in hexanes) to obtain (2-chloropyrimidin-5-yl)methyl methanesulfonate. MS: (ES) m/z calculated for C6H8ClN2O3S [M+H]+ 223.0. found 223.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19.13% | With phosphorus tribromide; In dichloromethane; at 20℃; | To a suspension of <strong>[1046816-75-4](2-chloropyrimidin-5-yl)methanol</strong> (330 mg, 2.283 mmol) in DCM (6.0 mL) was added a solution of PBr3 (0.323 ml, 3.42 mmol) in DCM (0.3 mL) dropwise. The resulting mixture was stirred at RT for overnight. The mixture was concentrated under reduced pressure and purified by ISCO (Hexanes/AcOEt, 0-100percent) to afford the title compound (Intermediate 197a, 110 mg, 0.437 mmol, 19.13 percent yield) as a white solid. LC-MS (Method A5): 1.72 min, [M + H]+= 252.8; 1H NMR (500 MHz, MeOH-i delta 8.67 (s, 2H), 4.68 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 130℃; for 3h;Microwave irradiation; | To a microwave reaction vial with terf-butyl azetidin-3-ylcarbamate hydrochloride (433 mg, 2.1 mmol) in acetonitrile (10 mL) was added (2-chloropyrimidin-5-yl)methanol (300 mg, 2.1 mmol) and N,N-diisopropylethylamine (1 .8 mL, 10 mmol). The mixture was heated in a microwave at 130 for 3 h, cooled and concentrated. The resulting residue was purified on silica gel eluting with a 30%-100% EtOAc:EtOH (3:1) in hexanes gradient to give the title compound (415 mg, 71 %) as a white solid. 1H NMR (400 MHz, CD3OD) delta 1 .47 (s, 9 H), 3.96 (dd, J = 9, 6 Hz, 2 H), 4.38 (t, J = 8 Hz, 2 H), 4.48 (s, 2 H), 4.48-4.57 (m, 1 H), 8.34 (s, 2 H); LC-MS (LC-ES) M+H = 281 . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.01% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -20 - 20℃; for 12h; | Compound II-1 (50.01 g, 0.347 mol, 1.0 e.q.) was dissolved in THF (500 mL), and compound III (75.39 g, 0.347 mol, 1.0 e.q.) was added.Triphenylphosphine (135.1 g, 0.347 mol, 1.0 e.q.), cooled to -20 ° C, DIAD (70.21 g, 0.347 mol, 1.0 e.q.) was added dropwise, and the reaction was stirred at room temperature for 12 h.The reaction solution was poured into water, extracted with EA and washed with saturated aqueous sodium hydrogen carbonate.After drying, the reaction solution was concentrated, and the precipitated solid was removed by crystallization with PE/EA. The reaction solution was concentrated to give Compound IV-1 as a yellow liquid, 71.43 g. The yield was 60.01percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With palladium diacetate; anhydrous sodium carbonate; dicyclohexyl [2’,4’,6’-tris(propan-2-yl)-[1,1‘-biphenyl]-2-yl]phosphane In 1,4-dioxane; lithium hydroxide monohydrate at 100℃; for 12h; |
Tags: 1046816-75-4 synthesis path| 1046816-75-4 SDS| 1046816-75-4 COA| 1046816-75-4 purity| 1046816-75-4 application| 1046816-75-4 NMR| 1046816-75-4 COA| 1046816-75-4 structure
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P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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