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ChemicalBook CAS DataBase List 4-Chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine
479633-63-1

4-Chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine synthesis

11synthesis methods
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (2kg, 12.96mol) and dichloromethane (40L) were added to the reaction flask at room temperature, stirred and dissolved. Triethylamine (3.88 kg, 38.4 mol) and 4-dimethylamino pyridine (157.6 g, 1.28 mol) were added in that order, and after stirring and dissolved, p-toluenesulfonyl chloride (2.6 kg, 13.6 mol) was added dropwise at 0 °C. The chloromethane (30 L) solution was added dropwise, and the mixture was stirred at room temperature for 30 min. After the TLC was applied, the mixture was washed with water (16L×3). 4-Chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (3.9 kg, yield 97.7%) was obtained after drying under reduced pressure.
4-Chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine
-

Yield:479633-63-1 97%

Reaction Conditions:

with sodium hydroxide in water;acetone at 0 - 20; for 6 h;

Steps:

1.1

EXAMPLE 13-((3Λ,4Λ)-4-Methyl-3-(methyl(7H-pyrrolo[2,3-rf]pyrimidin-4- yl)amino)piperidin-l-yl)-3-oxopropanenitrile mono citrate salt (CP-690550 citrate salt)Step 1[00151] 4-Chloro-7-tosyl-7H-pyrrolor2,3-6?pynmidine: At about O 0C, sodium hydroxide (2 mol/L in water, 8 mL, 1.20 equiv.) was added to a solution of 4- methylbenzene-1-sulfonyl chloride (2.7 g, 13.9 mmol, 1.10 equiv.) and 4-chloro- 7H-pyrrolo[2,3-J]pyrimidine (2 g, 12.8 mmol, 1.00 equiv.) in acetone (20 mL). The resulting solution was stirred at about 20 0C for about 6 hours. The solids were collected by filtration and washed with acetone/water to give the title product as a white solid (4.0 g; yield = 97%). 1H NMR (300 MHz, CDCl3) δ: 8.78 (s, IH), 8.11 (d, J = 8.4 Hz, 2H), 7.80 (d, J = 4.2 Hz, IH), 7.34 (d, J = 8.4 Hz, 2H), 7.73 (d, J = 4.2 Hz, IH), 2.42 (s, 3H). LC-MS: m/z = 308/310 (M+H)+.

References:

WO2010/123919,2010,A2 Location in patent:Page/Page column 49

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