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61727-34-2

61727-34-2 Structure

61727-34-2 Structure
IdentificationBack Directory
[Name]

5-PYRIMIDINEACETIC ACID, 4-CHLORO-2-(METHYLTHIO)-, ETHYL ESTER
[CAS]

61727-34-2
[Synonyms]

NSC 165400
Ethyl 4-chloro-2-(methylthio)pyrimidine-5-acetate
ethyl 2-(4-chloro-2-(Methylthio)pyriMidin-5-yl)acetate
Ethyl [4-chloro-2-(methylsulfanyl)pyrimidin-5-yl]acetate
Ethyl 2-(4-chloro-2-methylsulfanylpyrimidin-5-yl)acetate
4-Chloro-2-(methylthio)-5-pyrimidineacetic acid ethyl ester
5-PYRIMIDINEACETIC ACID, 4-CHLORO-2-(METHYLTHIO)-, ETHYL ESTER
(4-chloro-2-methylsulfanyl-pyrimidin-5-yl)-acetic acid ethyl ester
[Molecular Formula]

C9H11ClN2O2S
[MDL Number]

MFCD11977460
[MOL File]

61727-34-2.mol
[Molecular Weight]

246.71
Chemical PropertiesBack Directory
[Melting point ]

38-39 °C(Solv: ethanol (64-17-5); water (7732-18-5))
[Boiling point ]

345.8±27.0 °C(Predicted)
[density ]

1.32±0.1 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,2-8°C
[pka]

-0.82±0.29(Predicted)
[Appearance]

White to yellow <38°C Solid,>39°C Liquid
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H332-H335
[Precautionary statements ]

P261-P280-P305+P351+P338
[RIDADR ]

UN2811
[HS Code ]

2933599590
Hazard InformationBack Directory
[Uses]

Ethyl [4-Chloro-2-(methylsulfanyl)pyrimidin-5-yl]acetate is used in preparation of the dihydropyrrolopyrimidine-selective JAK2 inhibitors.
[Synthesis]

5-PYRIMIDINEACETIC ACID, 3,4-DIHYDRO-2-(METHYLTHIO)-4-OXO-, ETHYL ESTER

29571-44-6

5-PYRIMIDINEACETIC ACID, 4-CHLORO-2-(METHYLTHIO)-, ETHYL ESTER

61727-34-2

Step 3: General procedure for the synthesis of ethyl 4-chloro-2-methylthio-5-pyrimidineacetate from ethyl 2-(2-(methylthio)-6-oxo-1,6-dihydropyrimidin-5-yl)acetate: ethyl 2-(2-(methylthio)-6-oxo-1,6-dihydropyrimidin-5-yl)acetate (28.8 g, 0.128 mol) was dissolved in phosphorous triclosan (240 mL ) in the reaction and refluxed for 4 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The concentrated residue was co-evaporated twice with benzene to completely remove the residual phosphorous trichloride. Finally, it was purified by silica gel column chromatography (eluent: ethyl acetate-hexane, 1:3) to afford ethyl 4-chloro-2-(methylthio)pyrimidin-5-yl acetate (29.72 g, 95.5% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.32 (s, 1H), 4.13 (q, J=5.7 Hz, 2H), 3.62 (s, 2H), 2.52 (s, 3H), 1.21 (t, J=5.7 Hz, 3H).

[References]

[1] Patent: WO2009/152027, 2009, A1. Location in patent: Page/Page column 22; 25
[2] Patent: WO2017/176812, 2017, A1. Location in patent: Paragraph 0374
[3] Monatshefte fur Chemie, 2016, vol. 147, # 4, p. 767 - 773
[4] Patent: WO2016/22644, 2016, A1. Location in patent: Page/Page column 73
Spectrum DetailBack Directory
[Spectrum Detail]

5-PYRIMIDINEACETIC ACID, 4-CHLORO-2-(METHYLTHIO)-, ETHYL ESTER(61727-34-2)1HNMR
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