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[ CAS No. 672-41-3 ]

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2D
Chemical Structure| 672-41-3
Chemical Structure| 672-41-3
Structure of 672-41-3 *Storage: {[proInfo.prStorage]}

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Product Details of [ 672-41-3 ]

CAS No. :672-41-3MDL No. :MFCD08436657
Formula : C5H4F3N3 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :163.10Pubchem ID :22385756
Synonyms :

Computed Properties of [ 672-41-3 ]

TPSA : 51.8 H-Bond Acceptor Count : 6
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.20 Rotatable Bond Count : 0

Safety of [ 672-41-3 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 672-41-3 ]

  • Upstream synthesis route of [ 672-41-3 ]
  • Downstream synthetic route of [ 672-41-3 ]

[ 672-41-3 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 37552-81-1 ]
  • [ 672-41-3 ]
YieldReaction ConditionsOperation in experiment
98% With ammonia In water; acetonitrile at 25℃; for 12 h; Method 30
4-Amino-6-trifluoromethylpyrimidine
A solution of 4-chloro-6-trifluoromethylpyrimidine (1.7 g, 9.9 mmol) in CH3CN (50 ml) was treated with 25percent ammonia(aq) (80 ml).
The mixture was stirred at 25° C. for ~12 h.
The reaction mixture was quenched with H2O and extracted with EtOAc.
The organics were dried with NaCl(sat) and then Na2SO4(s).
The organics were removed under reduced pressure to give 1.5 g (98percent) of the title compound as a white solid. NMR: 6.80 (s, 1H); 7.52 (brs, 2H); 8.49 (s, 1H).
920 mg With ammonia In methanol at 70℃; for 15 h; Sealed tube Add 6-(trifluoromethyl)pyrimidin-4-ol (1.5 g, 9.15 mmol) and oxalyl chloride (2.3 mL, 22.9 mmol) to EtOAc (15 mL), then add 5 drops of DMF.
Heat the mixture to reflux for 2 hrs.
After reaction, partition between EtOAc and brine, separate the organic layer; dry the organic layer over anhydrous Na2SO4.
Transfer the organic solution to a sealed tube, add a solution of NH3 in methanol (7M, 10 mL), seal the tube, heat at 70° C. for 15 hrs.
Cool to room temperature; concentrate under reduced pressure to get the crude product.
Purification by chromatography (silica gel, EtOAc:PE=2:1) affords the target compound (920 mg, 61.3percent).
Reference: [1] Patent: US2009/170849, 2009, A1, . Location in patent: Page/Page column 14
[2] Patent: WO2014/176210, 2014, A1, . Location in patent: Paragraph 00236
[3] Patent: US2015/197511, 2015, A1, . Location in patent: Paragraph 0393; 0394
[4] Patent: WO2007/119055, 2007, A1, . Location in patent: Page/Page column 37
  • 2
  • [ 1546-78-7 ]
  • [ 672-41-3 ]
YieldReaction ConditionsOperation in experiment
14%
Stage #1: for 7 h; Heating / reflux
Stage #2: With ammonia In water at 20℃;
Preparation of 6-Trifluoromethyl-pyrimidin-4-ylamine; The procedure was derived from methods described in US 5,756,275 and WO 02/38569. In a 250 mL round bottom flask, 6-trifluorornethyl-4-pyrimidinol (10 g, 60.9 mmol) was dissolved in 70 mL phosphorus oxychloride (0.73 mol). The solution was heated at reflux for 7 h. The cooled reaction solution was then added gradually to 200 mL 30percent ammonium hydroxide, and the resulting mixture was stirred overnight at room temperature. The reaction mixture was extracted with ethyl acetate (2 x 100 mL), and the combined extracts were dried (MgSO4) and evaporated in vacuo to give 6-trifluoromethyl-pyrimidin-4-ylamiπe (1.4 g, yield 14percent) as a white solid. 1H NMR (400 MHz, DMSO-dβ) δ 8.50 (s, 1 H), 7.60 (broad s, 2 H), 6.90 (s, 1 H); LC-MS m/z 164.1 [M+Hf.
Reference: [1] Patent: WO2007/75650, 2007, A2, . Location in patent: Page/Page column 43
[2] Patent: US2015/197511, 2015, A1,
[3] Patent: WO2007/119055, 2007, A1,
  • 3
  • [ 1546-78-7 ]
  • [ 7664-41-7 ]
  • [ 672-41-3 ]
YieldReaction ConditionsOperation in experiment
61.3%
Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In ethyl acetate for 2 h; Reflux
Stage #2: at 70℃; for 15 h; Sealed tube
Add 6-(trifluoromethyl)pyrimidin-4-ol (1.5 g, 9.15 mmol) and oxalyl chloride (2.3 mL, 22.9 mmol) to EtOAc (15 mL), then add 5 drops of DMF. Heat the mixture to reflux for 2 hrs. After reaction, partition between EtOAc and brine, separate the organic layer; dry the organic layer over anhydrous Na2S04. Transfer the organic solution to a sealed tube, add a solution of NH3 in methanol (7M, lOmL), seal the tube, heat at 70°C for 15 hrs. Cool to room temperature; concentrate under reduced pressure to get the crude product. Purification by chromatography (silica gel, EtOAc:PE=2:l) affords the target compound (920 mg, 61.3percent).
Reference: [1] Patent: WO2014/418, 2014, A1, . Location in patent: Page/Page column 84
  • 4
  • [ 368-54-7 ]
  • [ 672-41-3 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 5744,5751
[2] Journal of the American Chemical Society, 1958, vol. 80, p. 5744,5751
  • 5
  • [ 1546-78-7 ]
  • [ 672-41-3 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 5744,5751
  • 6
  • [ 1513-72-0 ]
  • [ 672-41-3 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 5744,5751
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