Structure of 51421-99-9
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CAS No. : | 51421-99-9 |
Formula : | C5H5ClN2O |
M.W : | 144.56 |
SMILES Code : | ClC1=NC(=NC=C1)OC |
MDL No. : | MFCD09025734 |
InChI Key : | XCAMEGPUILTZSU-UHFFFAOYSA-N |
Pubchem ID : | 575230 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
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 | 0.0 |
Molar Refractivity | 33.53 |
TPSA ? Topological Polar Surface Area: Calculated from |
35.01 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.79 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.47 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.14 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.33 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.56 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.26 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.09 |
Solubility | 1.18 mg/ml ; 0.00813 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.81 |
Solubility | 2.23 mg/ml ; 0.0154 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.37 |
Solubility | 0.612 mg/ml ; 0.00424 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.14 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.8 |
* 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 |
---|---|---|
22% | a) 4-(4-(Trifluoromethyl)phenyl)pyrimidin-2(1H)-one (CAS Registry Number 1159816-20-2) A suspension of <strong>[51421-99-9]4-chloro-2-methoxypyrimidine</strong> (500 mg, 3.47 mmol), 4-(trifluoromethyl)phenylboronic acid (788 mg, 4.17 mmol), PdCl2(dppf) (283 mg, 0.347 mmol) and K2CO3 (958 mg, 6.94 mmol) in DMSO (10 mL) was degassed under reduced pressure for 45 min. The suspension was put under N2 and stirred at 95 C. for 20 h. The suspension was cooled, H2O was added and the suspension was filtered to afford a light colored solid. Flash chromatography on silica gel (hexanes/(1:1 EtOAc/hexanes), 100:0 to 0:100) afforded a white solid. The white solid was diluted with concentrated HCl solution (10 mL) and stirred at reflux for 4 h. The reaction was cooled, and the solution was neutralized with saturated NaHCO3 solution. The resulting suspension was filtered to afford 185 mg (22%) of the title compound as a white solid: ESI MS m/z 241 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 95℃; for 16h; | a) (E)-2-Methoxy-4-styrylpyrimidine A solution of <strong>[51421-99-9]4-chloro-2-methoxypyrimidine</strong> (0.36 g, 2.5 mmol), trans-2-phenylvinylboronic acid (0.56 g, 3.8 mmol) and potassium carbonate (0.69 g, 5.0 mmol) in DMSO (8.0 mL) was purged with argon for 5 min. 1,1'-Bis(diphenylphosphino)ferrocenedichloropalladium(II) (0.18 g, 0.25 mmol) was added to the above solution. The reaction mixture was purged with argon for 5 min and then heated at 95 C. for 16 h. The reaction solution was cooled to room temperature, diluted with ethyl acetate, washed with water (2*) and brine, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (silica gel hexanes/ethyl acetate 95:5 to 60:40) to afford the title compound (0.51 g, 96%) as a yellow solid: 1H NMR (500 MHz, CDCl3) delta 8.47 (d, J=5.0 Hz, 1H), 7.92 (d, J=16.0 Hz, 1H), 7.61-7.58 (m, 2H), 7.42-7.35 (m, 3H), 7.01 (d, J=16.0 Hz, 1H), 6.94 (d, J=5.0 Hz, 1H), 4.07 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 100℃; for 4h;Inert atmosphere; | a) 2-Methoxy-4-(6-(trifluoromethyl)pyridin-3-yl)pyrimidine A solution of <strong>[51421-99-9]4-chloro-2-methoxypyrimidine</strong> (0.50 g, 3.5 mmol), 2-trifluoromethyl)pyridine-5-boronic acid (1.0 g, 5.2 mmol) and potassium carbonate (0.95 g, 6.9 mmol) in DMSO was degassed with argon for 10 min. 1,1'-Bis(diphenylphosphino)ferrocenedichloropalladium(II) (0.26 g, 0.35 mmol) was then added to the above solution. The reaction mixture was degassed with argon for 5 min and then heated at 100 C. for 4 h. The reaction solution was cooled to room temperature, diluted with ethyl acetate, washed with water (2*) and brine, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (silica gel hexanes/ethyl acetate 95:5 to 50:50) to afford the title compound (0.80 g, 90%) as an off-white solid: 1H NMR (500 MHz, CDCl3) delta 9.37 (d, J=2.0 Hz, 1H), 8.69 (d, J=5.5 Hz, 1H), 8.61 (dd, J=8.0, 2.0 Hz, 1H), 7.83 (d, J=8.5 Hz, 1H), 7.44 (d, J=5.0 Hz, 1H), 4.12 (s 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dimethylimidazolium iodide; sodium hydride; In 1,4-dioxane; mineral oil; at 20℃;Reflux; | 159.2 2-Chloro-5-(2-methoxyDyrimidine-4-carbonyl)benzoic acid methyl esterA 60% suspension of NaH in mineral oil (51 mg) was added to a solution of 4-chloro-2- methoxypyrimidine (123 mg), intermediate 159.1 (170 mg) and dimethylimidazolium iodide (96 mg) in dioxane (35 mL). The reaction mixture was heated to reflux for 4h30 and ON at RT. It was diluted with water and extracted with EtOAc. The organic phase was dried over MgS04 and concentrated in vacuo. The crude was purified by CC (Hept/EtOAc 1/0 to 7/3) to give 49 mg of the titled compound as a light yellow solid.LC-MS (B): tR = 0.77 min; [M+H]+: 307.19 | |
49 mg | With sodium hydride; 1,3-dimethylimidazolim iodide; In 1,4-dioxane; mineral oil; at 20 - 30℃; | 159.2 2-Chloro-5-(2-methoxypyrimidine-4-carbonyl)benzoic acid methyl ester A 60% suspension of NaH in mineral oil (51 mg) was added to a solution of <strong>[51421-99-9]4-chloro-2-methoxypyrimidine</strong> (123 mg), intermediate 159.1 (170 mg) and dimethylimidazolium iodide (96 mg) in dioxane (35 mL). The reaction mixture was heated to reflux for 4 h30 and ON at RT. It was diluted with water and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated in vacuo. The crude was purified by CC (Hept/EtOAc 1/0 to 7/3) to give 49 mg of the titled compound as a light yellow solid. LC-MS (B): tR=0.77 min; [M+H]+: 307.19 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With caesium carbonate;palladium diacetate; XPhos; In 1,4-dioxane; at 100 - 140℃; for 72h;Inert atmosphere; Sealed tube; Microwave irradiation; | Palladium(II) acetate (4.2 mg, 0.019 mmol) was added to a stirred suspension of 2- phenoxymethyl-6H-imidazo[l,2-c]pyrimidin-5-one (150 mg, 0.62 mmol), 4-chloro-2- methoxy-pyrimidine (107.9 mg, 0.75 mmol), Cs2C03 (283.6 mg, 0.87 mmol) and 2- dicyclohexylphosphino-2',4',6'-triiso-propyl-l,l'-biphenyl (26.7 mg, 0.056 mmol) in 1,4- dioxane (2 mL) under nitrogen and in a sealed tube. The mixture was stirred at 100 C for 3 days and at 140 C for 15 minutes under microwave irradiation. The solvent was evaporated in vacuo and the crude product was purified by flash column chromatography (silica; AcOEt in DCM with a gradient of 0/100 to 100/0). The desired fractions were collected and the solvents evaporated in vacuo. The product was triturated with diethyl ether to yield 6-(2- methoxy-pyrimidin-4-yl)-2-phenoxymethyl-6H-imidazo[l,2-c]pyrimidin-5-one (43 mg, 20% yield) as a white solid. 1H NMR (400 MHz,CDCl3) delta ppm 4.09 (s, 3 H), 5.18 (d, J=0.9 Hz, 2 H), 6.77 (dd, J=8.2, 0.6 Hz, 1 H), 6.95 - 7.06 (m, 3 H), 7.27 - 7.36 (m, 2 H), 7.85 (d, J=0.7 Hz, 1 H), 7.91 (d, J=5.5 Hz, 1 H), 8.24 (d, J=8.1 Hz, 1 H), 8.65 (d, J=5.5 Hz, 1 H). |
20% | With palladium diacetate; caesium carbonate; XPhos; In 1,4-dioxane; at 100 - 140℃; for 72.25h;Inert atmosphere; Microwave irradiation; | Palladium(II)acetate (4.2 mg, 0.019 mmol) was added to a stirred suspension of 2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (150 mg, 0.62 mmol), <strong>[51421-99-9]4-chloro-2-methoxy-pyrimidine</strong> (107.9 mg, 0.75 mmol), Cs2CO3 (283.6 mg, 0.87 mmol) and 2-dicyclohexylphosphino-2',4',6'-triiso-propyl-1,1'-biphenyl (26.7 mg, 0.056 mmol) in 1,4-dioxane (2 mL) under nitrogen and in a sealed tube. The mixture was stirred at 100 C. for 3 days and at 140 C. for 15 minutes under microwave irradiation. The solvent was evaporated in vacuo and the crude product was purified by flash column chromatography (silica; AcOEt in DCM with a gradient of 0/100 to 100/0). The desired fractions were collected and the solvents evaporated in vacuo. The product was triturated with diethyl ether to yield 6-(2-methoxy-pyrimidin-4-yl)-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (43 mg, 20% yield) as a white solid. 1H NMR (400 MHz, CDCl3) delta ppm 4.09 (s, 3H), 5.18 (d, J=0.9 Hz, 2H), 6.77 (dd, J=8.2, 0.6 Hz, 1H), 6.95-7.06 (m, 3H), 7.27-7.36 (m, 2H), 7.85 (d, J=0.7 Hz, 1H), 7.91 (d, J=5.5 Hz, 1H), 8.24 (d, J=8.1 Hz, 1H), 8.65 (d, J=5.5 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.6 g | With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; | 6.01.12.01 4- 2-methoxy-pyrimidin-4-yl)-piperazine-l-carboxylic acid tert-butyl ester 1.3 g piperazine-l-carboxylic acid tert-butyl ester and 1.42 mL DIPEA were added to 1 g 2,4- dichlor-pyrimidine in 10 mL dichlormethane. The reaction was stirred over night at RT. The solvent was removed and the residue was purified by chromatography on silica gel (cyclohexane/ ethylacetate) to yield 1.6 g of the desired compound. Rt: 2.10 min (method I), (M+H)+: 299 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With palladium diacetate; caesium carbonate; XPhos; In 1,4-dioxane; at 100℃; for 24h; | [00587] Palladium (II) acetate (2.8 mg, 0.012 mmol) was added to a stirred suspension of 2-(benzyloxy)-6,7-dihydropyrazolo[l,5-a]pyrazin-4(5H)-one (0.1 g, 0.41 mmol), 4-chloro-2- methoxy-pyrimidine (0.120 g, 0.82 mmol), 2-dicyclohexylphosphino-2',4',6'- triisopropylbiphenyl (17.7 mg, 0.037 mmol) and CS2CO3 (0.19 g, 0.58 mmol) in 1,4-dioxane (2 mL). The mixture was stirred at 100 C for 24 hours. The solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; 7 M solution of ammonia in MeOH in DCM 0/100 to 95/5). The desired fractions were collected, the solvents evaporated in vacuo and the residue triturated with diethyl ether to yield 2-(benzyloxy)-5-(2- methoxypyrimidin-4-yl)-6,7-dihydropyrazolo[l,5-a]pyrazin-4(5H)-one (51 mg, 35% yield) as a white solid. dsHnNsOs. 1H NMR (500 MHz, CDC13) delta ppm 4.03 (s, 3 H), 4.33 (dd, J=6.6, 5.2 Hz, 2 H), 4.64 (dd, J=6.6, 5.2 Hz, 2 H), 5.23 (s, 2 H), 6.40 (s, 1 H), 7.31 - 7.36 (m, 1 H), 7.39 (t, J=7.4 Hz, 2 H), 7.42 - 7.48 (m, 2 H), 7.89 (d, J=5.8 Hz, 1 H), 8.44 (d, J=5.8 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: This compound was prepared using a method analogousto that of Example 102 (intermediate 102.1 ), <strong>[51421-99-9]4-chloro-2-methoxypyrimidine</strong> replacing 2,6-difluoropyridine exceptthat the reaction mixture was stirred for 1 hat 80 C. then for18 hat RT and that the product precipitated out off the aqueousphase after acidification and was isolated by filtration LC-MS (B): tR=0.60 min; [M+H]+: 281.07 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: This compound was prepared using a method analogousto that of Example 102 (intermediate 102.1 ), <strong>[51421-99-9]4-chloro-2-methoxypyrimidine</strong> replacing 2,6-difluoropyridine andintermediate 132.4 replacing 2-chloro-5-hydroxybenzoicacid except that the reaction mixture was stirred for 30 min at80 C. LC-MS (B): tR=0.65 min; [M+H]+: 297.04 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
INTERMEDIATE 62 4-("3-Bromo-4-fluoro-lH"-pyrazol-l-vn-2-methoxypyrimidine To a solution of 3-bromo-4-fluoro-lH-pyrazole (500 mg, 3.03 mmol) in anhydrous DMSO (6 mL) was added NaH (133 mg, 3.13 mmol) at 0C. The mixture was stirred for 30 min at 0 C, followed by the addition of <strong>[51421-99-9]4-chloro-2-methoxypyrimidine</strong> (438 mg, 3.03 mmol) in DMSO (2 mL). The resulting mixture was stirred at 90 C overnight. The mixture was cooled to room temperature, quenched with water (10 mL) and extracted with EtOAc (40 mL x 3). The organic layer was collected and dried over Na2S04. The solvent was removed in vacuo to give the crude product. This was purified by flash chromatography (ISCO Combiflash, 24g, Biotage Si column, ~60 mL/min, 100% hexanes 5 min, gradient to 100% EtOAc in hexanes 15 min) to afford 4-(3-bromo-4-fluoro-lH-pyrazol-l-yl)-2-methoxypyrimidine. LCMS calc. = 274.98; found = 274.90 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With hydrazine hydrate; In ethanol; at 85℃; for 1h;Inert atmosphere; | Step 59.1: 4-hydrazinyl-2-methoxypyrimidine To a stirred solution of 526 <strong>[51421-99-9]4-chloro-2-methoxypyrimidine</strong> (5.7 g, 39.4 mmol) in EtOH (100 mL) under Ar was added hydrazine hydrate (3.83 mL, 79 mmol) and the reaction mixture was heated up and stirred at 85 C. for 1 hr. Volatiles were removed under reduced pressure and the resulting crude material was purified by silica gel column chromatography (CH2Cl2/MeOH/1-5%/NH3 1%) to afford the title product (4.40 g, 31.4 mmol, 80% yield) as white solid. ESI-MS: 141 [M+H]+ (LC-MS 2); Rf=0.47 (CH2Cl2/MeOH 9:1). |
80% | With hydrazine hydrate; In ethanol; at 58℃; for 1h;Inert atmosphere; | To a stirred solution of <strong>[51421-99-9]4-chloro-2-methoxypyrimidine</strong> (5.7 g, 39.4 mmol) in EtOH (100 mL)under Ar was added hydrazine hydrate (3.83 mL, 79 mmol) and the reaction mixture washeated up and stirred at 85C for 1 hr. Volatiles were removed under reduced pressure and the resulting crude material was purified by silica gel column chromatography (CH2CI2/MeOH/1- 5%/NH3 1%) to afford the title product (4.40 g, 31.4 mmol, 80% yield) as white solid. ESl-MS:141 [M+H] (LC-MS 2); R = 0.47 (CH2CI2/MeOH 9:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In ethanol; toluene; at 90℃; for 16h;Inert atmosphere; | Step 1 : tert-Butyl (3-(3-(2-methoxypyrimidin-4-yl)phenoxy)-3- phenylpropyl)(methyl)carbamate. (0379) A Radley tube was charged with tert-butyl methyl(3-phenyl-3-(3-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)phenoxy)propyl)carbamate (Intermediate 1 , 200 mg, 0.163 mmol), <strong>[51421-99-9]4-chloro-2-methoxypyrimidine</strong> (250 mg, 1 .73 mmol), PdCI2(dppf)-CH2Cl2 (13.3 mg, 0.016 mmol) and purged with argon. Degassed Na2CC>3 solution (0.4 M, 0.41 mL, 0.163 mmol) was added followed by toluene/EtOH (9/1 , 7 mL) and the reaction mixture heated at 90 C for 16 h under argon atmosphere. The layers were separated and the organic phase was washed with water and concentrated to dryness under reduced pressure. The residue was purified by combiflash chromatography (neutral alumina, CH/EtOAc up to 100%) to give the title compound (28 mg, 38% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [(2-di-tert-butylphosphino-2?,4?,6?-triisopropyl-1, 1?-biphenyl)-2-(2?-amino-1,1?-biphenyl)] palladium(II) methanesulfonate; sodium t-butanolate; In tetrahydrofuran; | To a mixture of tert-butyl (S)-2-amino-4-(((R)-2-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoate (101 mg, 232 mumol) and <strong>[51421-99-9]4-chloro-2-methoxypyrimidine</strong> (28 mg, 194 mol) in t-AmOH (2 mL) was added 2.0M t-BuONa in THF (194 muL, 388 muL) and tBuXPhos-Pd-G3 (15 mg, 19 mumol) and the resulting mixture was heated to 100 C. for 15 h, cooled to rt, and then concentrated in vacuo to give a ((S)-tert-butyl 4-(((R)-2-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino)-2-((2-methoxypyrimidin-4-yl) amino) butanoate intermediate, LCMS (ESI+): m/z=543.4 (M+H)+, which was used without further purification. Of the butanoate intermediate, 100 mg, 184 mumol, was taken up in DCM (2 mL) was added TFA (333 muL) and the resulting mixture was stirred at rt for 3 h and then concentrated in vacuo. The crude residue was purified by reverse phase prep-HPLC to give the title compound. LCMS (ESI+): m/z=487.3 (M+H)+. 1H NMR (400 MHz, DMSO-d6) delta ppm 7.81 (br s, 1H) 7.47-7.62 (m, 1H) 7.01 (br d, J=7.21 Hz, 1H) 6.35 (br d, J=13.57 Hz, 1H) 6.18-6.28 (m, 2H) 4.31 (br s, 1H) 3.73 (s, 3H) 3.23 (br s, 2H) 3.19 (s, 4H) 2.67 (br s, 1H) 2.59 (brt, J=6.11 Hz, 4H) 2.31-2.43 (m, 5H) 1.86-1.97 (m, 1H) 1.71-1.78 (m, 3H) 1.54 (br dd, J=14.73, 7.40 Hz, 2H) 1.41 (br d, J=7.21 Hz, 2H) 1.03 (t, J=5.50 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [(2-di-tert-butylphosphino-2?,4?,6?-triisopropyl-1, 1?-biphenyl)-2-(2?-amino-1,1?-biphenyl)] palladium(II) methanesulfonate; sodium t-butanolate; In tetrahydrofuran; at 100℃; for 15h; | To a mixture of (S)-tert-butyl 2-amino-4-(((S)-2-fluoro-3-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoate (150 mg, 331 mumol) and <strong>[51421-99-9]4-chloro-2-methoxy-pyrimidine</strong> (40 mg, 276 mol) in t-AmOH (3 mL) then was added 2.0M t-BuONa in THF (276 muL, 552 mumol) and t-BuXPhos-Pd-G3 (22 mg, 28 mumol) and the resulting mixture was heated to 100 C. for 15 h, cooled to rt, and then concentrated in vacuo to give the title compound that was used without further purification. LCMS (ESI+): m/z=561.5 (M+H)+ |
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