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Chemistry
Heterocyclic Building Blocks
Pyrimidines
(S)-3-(2-Chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks Asymmetric Synthesis
Pyrimidines
Oxazolidines Chlorides Amides Chiral Building Blocks

[ CAS No. 1429180-81-3 ] (S)-3-(2-Chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one

Cat. No.: A446814
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Chemical Structure| 1429180-81-3
Chemical Structure| 1429180-81-3
 Structure of 1429180-81-3
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Product Details of [ 1429180-81-3 ]

CAS No. :1429180-81-3 MDL No. :
Formula : C10H12ClN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 241.67 Pubchem ID :-
Synonyms :

Safety of [ 1429180-81-3 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H311-H331 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1429180-81-3 ]

* 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.

  • Downstream synthetic route of [ 1429180-81-3 ]

[ 1429180-81-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1429180-81-3 ]
  • [ 68285-27-8 ]
  • [ 1429176-16-8 ]
  • [ 1429176-17-9 ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide; at 110℃; for 1.5h; Examples 171 and 172A solution of (S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one (106 mg, 0.439 mmol) and 1 -(3-fluorophenyl)ethanamine (196 mg, 1 .41 mmol, 3.21 equiv) in DMSO (1 mL) was heated at 1 10 C for 1 ? h. The reaction mixture was diluted with EtOAc (8 mL) and washed with water (30 mL). After separation, the aqueous phase was extracted with EtOAc (3 x 8 mL). Combined organics were dried over Na2S04, filtered and concentrated. Silica gel column chromatography (EtOAc/Heptane 10 to 50%) provided (S)-3-(2-((/?)-1 -(3-fluorophenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one and (S)-3-(2-((S)-1-(3-fluorophenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2- one.Example 171 first eluted product (28 mg) 1 H NMR (400 MHz, CD3OD) ? 8.1 1 (d, J = 5.8 Hz, 1 H), 7.36 - 7.27 (m, 2 H), 7.16 (d, J = 7.6 Hz, 1 H), 7.07 (dt, J = 10, 2.0 Hz, 1 H), 6.92 - 6.88 (m, 1 H), 4.98 - 4.93 (m, 1 H), 4.42 (br s, 1 H), 4.32 (dd, J = 9.1 , 2.8 Hz, 1 H), 4.26 (t, J = 8.7 Hz, 1 H), 2.64 (dtd, J = 14, 7.1 , 3.5 Hz, 1 H), 1 .50 (d, J = 7.0 Hz, 3 H), 0.98 (d, J = 7.1 Hz, 3 H), 0.85 (d, J = 7.0 Hz, 3 H); HRMS(B) m/z 345.1729 (M + H)+. Example 172 second eluted product (22 mg) 1H NMR (400 MHz, CD3OD) ? 8.13 (d, J = 5.7 Hz, 1 H), 7.36 (d, J = 5.8 Hz, 1 H), 7.29 (td, J = 8.1 , 6.1 Hz, 1 H), 7.13 (d, J = 7.6 Hz, 1 H), 7.06 - 7.04 (m, 1 H), 6.94 - 6.87 (m, 1 H), 5.03 (q, J = 7.1 Hz, 1 H), 4.64 (br s, 1 H), 4.34 - 4.26 (m, 2 H), 1 .79 (br s, 1 H), 1 .50 (d, J = 7.1 Hz, 3 H), 0.70 (br s, 3 H), 0.58 (br s, 3 H); HRMS(B) m/z 345.1727 (M + H)+.
Reference： [1]Patent: WO2013/46136,2013,A1 .Location in patent: Page/Page column 163; 164
  • 2
  • [ 1429180-81-3 ]
  • [ 74877-07-9 ]
  • [ 1429176-22-6 ]
  • [ 1429176-23-7 ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide; at 110℃; for 1.5h; Examples 177 and 178A solution of (S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one (93 mg, 0.38 mmol) and 1 -(3,4-dichlorophenyl)ethanamine (73.1 mg, 0.385 mmol, 1 .0 equiv) in DMSO (1 mL) was heated at 1 10 C for 1 ? h. The reaction mixture was diluted with EtOAc (8 mL) and washed with water (30 mL). After separation, the aqueous phase was extracted with EtOAc (3 x 8 mL). Combined organics were dried over Na2S04, filtered and concentrated. Silica gel column chromatography (EtOAc/Heptane 10 to 50%) provided (S)-3-(2-((/?)-1 -(3,4-dichlorophenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2- one and (S)-3-(2-((S)-1-(3,4-dichlorophenyl)ethylamino)pyrimidin-4-yl)-4- isopropyloxazolidin-2-one.Example 177 first eluted product (21 mg) 1H NMR (400 MHz, CD3OD) ? 8.12 (d, J = 5.8 Hz, 1 H), 7.50 (d, J = 2.0 Hz, 1 H), 7.44 (d, J = 8.2 Hz, 1 H), 7.37 (d, J = 5.8 Hz, 1 H), 7.28 (dd, J = 8.6, 2.0 Hz, 1 H), 4.94 - 4.88 (m, 1 H), 4.43 (br s, 1 H), 4.35 - 4.26 (m, 2 H), 2.68 - 2.60 (m, 1 H), 1 .50 (d, J = 7.1 Hz, 3 H), 0.99 (d, J = 7.1 Hz, 3 H), 0.85 (d, J = 7.1 Hz, 3 H); HRMS(B) m/z 395.1035 (M + H)+.Example 178 second eluted product (28 mg) 1H NMR (400 MHz, CD3OD) ? 8.15 (d, J = 5.8 Hz, 1 H), 7.47 - 7.42 (m, 2 H), 7.37 (d, J = 5.8 Hz, 1 H), 7.25 (dd, J = 8.1 , 2.0 Hz, 1 H), 5.01 - 4.96 (m, 1 H), 4.61 (br s, 1 H), 4.34 - 4.26 (m, 2 H), 1.72 (br s, 1 H), 1 .50 (d, J = 7.1 Hz, 3 H), 0.67 (br s, 3 H), 0.60 (br s, 3 H); HRMS(B) m/z 395.1044 (M + H)+.
Reference： [1]Patent: WO2013/46136,2013,A1 .Location in patent: Page/Page column 165; 166

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Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling
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