* 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.
2-(2-Chloro-pyrimidin-5-yl)-1-propyl-1H-benzoimidazole A suspension of <strong>[38324-83-3]2-hydroxy-pyrimidine-5-carboxylic acid</strong> (300 mg, 2.14 mmol) [J. Arukwe, K. Undheim, Acta. Chem. Scand. (1986) B40, 764-767], in POCl3 (20 ml) was heated to 80 C. for 16 h. The excess of POCl3 was evaporated and the residue was dried in HV for 2 h. The crude product was then taken up in anhydrous THF (30 ml), treated with N-propyl-benzene-1,2-diamine (354 mg, 2.36 mmol) and the solution was stirred for 1 h at RT. The mixture was then concentrated in vacuo. Purification by flash chromatography (100:0 to 75:25) afforded 2-(2-chloro-pyrimidin-5-yl)-1-propyl-1H-benzoimidazole (63 mg, 11%). UPLC (5-100% CH3CN): tR=0.974 min, MS (ES+): 273 [M+1].
With trichlorophosphate; at 80.0℃; for 48h;
7-Chloro-2-(2-chloro-pyrimidin-5-yl)-1-propyl-1H-benzoimidazole A suspension of <strong>[38324-83-3]2-hydroxy-pyrimidine-5-carboxylic acid</strong> (3.25 g, 23.2 mmol) [J. Arukwe, K. Undheim (1986) Acta. Chem. Scand., B40, 764-767], in POCl3 (100 ml) was heated to 80 C. for 48 h. The excess of POCl3 was evaporated and the residue was dried in HV for 2 h. The crude product was then taken up in anhydrous THF (30 ml), treated with 3-chloro-N-2-propyl-benzene-1,2-diamine (4.35 g, 23.6 mmol) and the solution was stirred for 20 h at RT. The mixture was then concentrated in vacuo. Purification by flash chromatography (DCM/MeOH 100:0 to 85:15) provided 7-chloro-2-(2-chloro-pyrimidin-5-yl)-1-propyl-1H-benzoimidazole (40% pure, 8.0 g, 46%). UPLC (5-100% CH3CN): tR=1.462 min, MS (ES+): 307 [M+1].
With trichlorophosphate; at 80.0℃; for 16 - 48h;Product distribution / selectivity;
2-(2-Chloro-pyrimidin-5-yl)-1 -propyl-1 H-benzoimidazoleA suspension of <strong>[38324-83-3]2-hydroxy-pyrimidine-5-carboxylic acid</strong> (300 mg, 2.14 mmol) [J. Arukwe, K. Undheim, Acta. Chem. Scand. (1986) B40, 764-767], in POCI3 (20 ml) was heated to 80 0C for 16 h. The excess of POCI3 was evaporated and the residue was dried in HV for 2 h. 7-Chloro-2-(2-chloro-pyrimidin-5-yl)-1 -propyl-1 H-benzoimidazoleA suspension of <strong>[38324-83-3]2-hydroxy-pyrimidine-5-carboxylic acid</strong> (3.25 g, 23.2 mmol) [J. Arukwe, K.Undheim (1986) Acta. Chem. Scand., B40, 764-767], in POCI3 (100 ml) was heated to 80 0C for 48 h. The excess of POCI3 was evaporated and the residue was dried in HV for 2 h.
(2R,4R)-4-amino-5-biphenyl-4-yl-2-hydroxypentanoic acid ethyl ester hydrochloride[ No CAS ]
[ 38324-83-3 ]
[ 76-05-1 ]
[ 1383006-34-5 ]
Yield
Reaction Conditions
Operation in experiment
(2R,4R)-4-Amino-5-biphenyl-4-yl-2-hydroxypentanoic acid ethyl ester (HCl salt; 200 mg, 572 mumol, 1.0 eq.) and <strong>[38324-83-3]2-hydroxypyrimidine-5-carboxylic acid</strong> (88.1 mg, 629 mumol) were suspended in DMF (5.0 mL). HATU (239 mg, 629 mumol) was added followed by DIPEA (299 muL), and the resulting mixture was stirred at room temperature until the reaction was complete (2 hours). The mixture was divided into two equal portions and both solutions were concentrated. One portion was purified by preparative HPLC (10-70% MeCN/H2O) to produce compound A as a TFA salt (59.2 mg). MS m/z [M+H]+ calc'd for C24H25N3O5, 436.18. found 436.4.
With water; potassium hydroxide; In 1,4-dioxane;Inert atmosphere; Reflux;
Under nitrogen protection, 2-chloro-5-bromopyrimidine (19.3 g, 0.1 mol) and 35 mL of diethoxymethane were added to a three-neck reaction flask. Then cool down to -70 C to -60 C, A 2.2 M n-hexyllithium/hexane solution (48 mL, 0.11 mol) was initially added dropwise. After the addition is completed, the incubation reaction is continued for 1 hour. Then start adding Boc2O (22.9g, 0.105mol) The solution dissolved in diethoxyhexane (35 mL) was allowed to stand for 2 hours after the completion of the dropwise addition. Sampling detection reaction is over, the reaction was quenched by the addition of water. After layering, the organic layer was spun dry, and 2 M aqueous KOH (150 mL, 0.3 mol) and dioxane (110 mL) were added to warm to reflux for 5-6 hours.Then add 10% hydrochloric acid to adjust the pH<1 and stir the reaction for 3-4 hours, then add 1M potassium hydroxide to adjust the pH=4-5, layer, and wash the organic layer with saturated brine twice. Dry over anhydrous magnesium sulfate. Filter to dry the solvent, it is recrystallized by adding an ethanol/water mixed solvent, and dried under vacuum. 10.8 g of an off-white solid 2-hydroxypyrimidine-5-carboxylic acid was obtained, HPLC: 99.9%, yield 77%.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
