ChemicalBook CAS DataBase List 4-Chloro-2-methyl-1H-pyrrolo[2,3-d]pyrimidine

4-Chloro-2-methyl-1H-pyrrolo[2,3-d]pyrimidine synthesis

3synthesis methods

Product Name:4-Chloro-2-methyl-1H-pyrrolo[2,3-d]pyrimidine
CAS Number:71149-52-5
Molecular formula:C7H6ClN3
Molecular Weight:167.6

4H-Pyrrolo[2,3-d]pyrimidin-4-one, 1,7-dihydro-2-methyl- (9CI)

89792-11-0

71149-52-5

General procedure for the synthesis of 4-chloro-2-methyl-1H-pyrrolo[2,3-d]pyrimidine using 2-methyl-1H-pyrrolo[2,3-d]pyrimidin-4(7H)-one as starting material: 90 mg (0.60 mmol) of hydroxypyrrolo[pyrimidin-4(7H)-one was suspended in 2 mL of phosphorochloridic acid chloride, and the reaction was heated and refluxed for 2 hours. Upon completion of the reaction, excess phosphorus trichloride was removed by distillation under reduced pressure. The residue was carefully quenched with an ice water bath and subsequently extracted with ethyl acetate. The organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel fast column chromatography (eluent: 10% methanol/dichloromethane) to afford the target compound 4-chloro-2-methyl-1H-pyrrolo[2,3-d]pyrimidine as a colorless solid (86 mg, 85% yield). Mass spectrometry result: (M + H)+ m/z = 168.

89792-11-0
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$45.00/10mg

71149-52-5
130 suppliers
$36.00/1 / G

Yield: 95.8%

Reaction Conditions:

with tetraethylammonium chloride;trichlorophosphate at 60 - 80; for 0.5 h;

Steps:

6 Example 6: Preparation of 2-methyl-4-chloropyrrolopyrimidine.
A 2L three-necked flask is equipped with a thermometer and a condenser,Add 184g of phosphorus oxychloride, 16.6g of tetraethylammonium chloride, and warm up to 60 ,Add 149g of 2-methyl-4-hydroxypyrrolopyrimidine in portions and warm to 80 ° C,Incubate the reaction for 30 minutes, HPLC traces the reaction of the raw materials to completion, and lower the temperature to 30 ° C.Prepare 2 liters of 10% sodium hydroxide solution, slowly add the reaction solution to extract,Precipitate solid, filter by suction to get semi-finished product, recrystallize ethyl ester,The finished product was 161g after drying, and the yield was 95.8%.

References:

Anqing Bo Man Biological Co., Ltd.;Chen Jia;He Xueyin;Liu Pengcheng CN110950806, 2020, A Location in patent:Paragraph 0031-0034

2-METHYL-7H-PYRROLO[2,3-D]PYRIMIDIN-4-OL

1314922-47-8
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71149-52-5
130 suppliers
$36.00/1 / G

References

52133-67-2 Synthesis

52133-67-2
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$8.00/1g

71149-52-5
130 suppliers
$36.00/1 / G

References

4-Chloro-2-methyl-1H-pyrrolo[2,3-d]pyrimidine Related Search:

Methylparaben 1-Methylpyrrolidine N-Methyl-2-pyrrolidone Methyl salicylate Pyrimidine Methanol 4-CHLORO-2-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE