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289042-11-1

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Basic Information
CAS No.: 289042-11-1
Name: Methyl 4-(4-fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl)amino]pyrimidine-5-carboxylate
Article Data: 11
Molecular Structure:
Molecular Structure of 289042-11-1 (Methyl 4-(4-fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl)amino]pyrimidine-5-carboxylate)
Formula: C17H20FN3O4S
Molecular Weight: 381.428
Synonyms: 4-(4-Fluorophenyl)-6-isopropyl-2-[(methanesulfonyl)methylamino]pyrimidine-5-carboxylicacid methyl ester;Rosuvastatin intermediate R-1-1;(Carboxylate) 4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonyl amino)pyrimidine-5-carboxylate;4-(4-Fluorophenyl)-6-isopropyl-2-(n-methyl-N-methylsulfonylamino)pyrimidine-5-carboxylate;
EINECS: 608-290-6
Density: 1.305 g/cm3
Boiling Point: 551.956 °C at 760 mmHg
Flash Point: 287.613 °C
Appearance: White or off-white powder
PSA: 97.84000
LogP: 3.66930
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Synthetic route

4-(4-fluorophenyl)-6-isopropyl-5-methoxycarbonyl-3,4-dihydropyrimidine-2(1H)-one

1184-85-6

N-methylmethane sulphonamide

289042-11-1

methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate

Conditions
ConditionsYield
Stage #1: methyl 4-(4-fluorophenyl)-2-hydroxy-6-isopropylpyrimidine-5-carboxylate With potassium carbonate; p-toluenesulfonyl chloride In acetic acid butyl ester at 45℃; for 0.5h;
Stage #2: N-methylmethane sulphonamide With potassium carbonate In acetic acid butyl ester at 125℃; for 3h;		94%
1184-85-6

N-methylmethane sulphonamide

488798-38-5

2-chloro-4-(4-fluoro-phenyl)-6-isopropyl-pyrimidine-5-carboxylic acid methyl ester

289042-11-1

methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate

Conditions
ConditionsYield
Stage #1: N-methylmethane sulphonamide With sodium hydride In acetonitrile; mineral oil for 0.0833333h;
Stage #2: 2-chloro-4-(4-fluoro-phenyl)-6-isopropyl-pyrimidine-5-carboxylic acid methyl ester In acetonitrile; mineral oil for 7h; Reagent/catalyst; Solvent; Reflux;		93.2%
799842-06-1

4-(4-fluorophenyl)-6-isopropyl-2-(methylsulfonyl)pyrimidine-5-carboxylic acid methyl ester

41881-75-8

sodium salt of N-methyl-N-methylsulfonylamine

289042-11-1

methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 30℃; for 1h;92.42%
799842-06-1

4-(4-fluorophenyl)-6-isopropyl-2-(methylsulfonyl)pyrimidine-5-carboxylic acid methyl ester

1184-85-6

N-methylmethane sulphonamide

289042-11-1

methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 25 - 85℃; for 2.5 - 3h; Product distribution / selectivity; Heating / reflux;87.93%
With potassium carbonate In acetic acid butyl ester at 90℃; for 3h; Product distribution / selectivity;
160009-36-9

methyl 4-(4-fluorophenyl)-6-isopropyl-2-(methylamino)pyrimidine-5-carboxylate

124-63-0

methanesulfonyl chloride

289042-11-1

methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate

Conditions
ConditionsYield
Stage #1: methyl 4-(4-fluorophenyl)-6-isopropyl-2-(methylamino)pyrimidine-5-carboxylate With sodium tert-pentoxide In 1,2-dimethoxyethane at 20℃; for 1h; Inert atmosphere;
Stage #2: methanesulfonyl chloride In 1,2-dimethoxyethane at -10℃; for 1h;		78%
Stage #1: methyl 4-(4-fluorophenyl)-6-isopropyl-2-(methylamino)pyrimidine-5-carboxylate With sodium tert-pentoxide In 1,2-dimethoxyethane at 20℃; for 0.5h;
Stage #2: methanesulfonyl chloride In 1,2-dimethoxyethane at -10℃; for 0.5h;		76%
With n-butyllithium In tetrahydrofuran; hexane at -75 - -70℃;63%
Stage #1: methyl 4-(4-fluorophenyl)-6-isopropyl-2-(methylamino)pyrimidine-5-carboxylate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: methanesulfonyl chloride In N,N-dimethyl-formamide for 1h; Product distribution / selectivity;

methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate

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sodium tert-pentoxide

506-77-4

cyanogen chloride

289042-11-1

methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate

Conditions
ConditionsYield
In water74.1%
...Expand

methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate

1184-85-6

N-methylmethane sulphonamide

506-77-4

cyanogen chloride

289042-11-1

methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate

Conditions
ConditionsYield
With sodium t-butanolate In methanol; water; tert-butyl alcohol56.3%
In N,N-dimethyl acetamide; water; acetone29% [concentration (GC)
In N,N-dimethyl acetamide; water; acetone30.2% [concentration (GC)
In water; acetone
...Expand
317806-76-1

N-cyano-N-methylmethanesulphonamide

methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate

1184-85-6

N-methylmethane sulphonamide

289042-11-1

methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate

Conditions
ConditionsYield
With sodium t-butanolate In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; tert-butyl alcohol52.1%
...Expand
317806-76-1

N-cyano-N-methylmethanesulphonamide

methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate

289042-11-1

methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate

Conditions
ConditionsYield
In N,N-dimethyl acetamide; water27%
In N,N-dimethyl acetamide; water
titanium tetrachloride In water; toluene13.5% [concentration (HPLC)

methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate

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N-methylmethane sulphonamide

127-19-5

N,N-dimethyl acetamide

506-77-4

cyanogen chloride

289042-11-1

methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate

Conditions
ConditionsYield
In water22%
...Expand
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Chemistry


Systematic Name: Methyl 4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]pyrimidine-5-carboxylate
Molecular Formula: C17H20FN3O4S
Molecular Weight: 381.42 g/mol
Canonical SMILES: O=S(=O)(N(c1nc(c(c(n1)C(C)C)C(=O)OC)c2ccc(F)cc2)C)C
InChI: InChI=1/C17H20FN3O4S/c1-10(2)14-13(16(22)25-4)15(11-6-8-12(18)9-7-11)20-17(19-14)21(3)26(5,23)24/h6-10H,1-5H3
Product Categories: Intermediatesofrosuvastatincalcium; Rosuvastatin Calcium and its intermediates
Molar Volume: 292.364 cm3 
Polarizability: 37.303 10-24 cm3 
Surface Tension: 50.963 dyne/cm 
Density: 1.305 g/cm3 
Flash Point: 287.613 °C 
Enthalpy of Vaporization: 83.241 kJ/mol 
Boiling Point: 551.956 °C at 760 mmHg 
Vapour Pressure of Methyl 4-(4-fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl)amino]pyrimidine-5-carboxylate (CAS NO.289042-11-1): 0 mmHg at 25 °C

Specification

  Methyl 4-(4-fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl)amino]pyrimidine-5-carboxylate (CAS NO.289042-11-1), its Synonyms are 4-(4-Fluorophenyl)-6-isopropyl-2-[(methanesulfonyl)methylamino]pyrimidine-5-carboxylic acid methyl ester ; Rosuvastatin intermediate R-1-1 ;4-(4-Fluorophenyl)-6-isopropyl-2-(n-methyl-N-methylsulfonylamino)pyrimidine-5-carboxylate ; (Carboxylate) 4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonyl amino)pyrimidine-5-carboxylate .