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Chemical Structure| 186454-70-6

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Product Details of [ 186454-70-6 ]

CAS No. :186454-70-6
Formula : C6H5N3O
M.W : 135.12
SMILES Code : NC1=C2C(OC=C2)=NC=N1
MDL No. :MFCD09834959
InChI Key :JPIPZNJBXFDXHH-UHFFFAOYSA-N
Pubchem ID :9898839

Safety of [ 186454-70-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 186454-70-6 ]

* 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.

  • Upstream synthesis route of [ 186454-70-6 ]
  • Downstream synthetic route of [ 186454-70-6 ]

[ 186454-70-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 186454-70-6 ]
  • [ 918340-51-9 ]
YieldReaction ConditionsOperation in experiment
40%
Stage #1: With chloro-trimethyl-silane; tert.-butylnitrite In acetonitrile at 50℃; for 1.5 h;
Stage #2: With sodium hydroxide In water; acetonitrile
4-Chlorofuro[2,3,cflpyrimidine was obtained via modified Sandmeyer reaction25 with 4-amino-furopyrimidine 25.26(25) (a) For the modified Sandmeyer reaction, see: (a) Bracher, F.; Daab, J. Eur. J. Org. Chem. 2002, 2288. (b)Doyle, M. P.; Siegfiied, B.; Dellaria, J. F. J. Org. Chem. 1977, 42, 2426.(26) Nakano, M.; Maeda, Y. WO 2005061516 Al 20050707 CAN 143:115566. EPO <DP n="82"/>The mixture of 4-amino-furopyrimidme 25 (303 mg, 2.24 mmol), tert-butyl nitrite (5.3 niL, 44.6 mmol), TMSCl (1.4 mL, 11.07 mmol) in acetonitrile (5.0 mL) was stirred at 50 0C for 1.5 h. After this period, the mixture was quenched with IN NaOH and the aqueous phase was thoroughly extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography with 10percent EtOAc/hexanes to give 26 (139 mg, 40percent).1H NMR (500 MHz, CDCl3, δ): 8.68 (s, IH), 7.72 (d, J= 2.5 Hz5 IH), 6.84 (d, J = 2.5 Hz5 IH). 13C NMR (125 MHz5 CDCl3, δ): 167.1, 154.0, 153.5, 146.0, 177.9, 104.7. MS m/z (relative intensity) 154 (M+, 100), 119 (37), 98 (21).
22% With chloro-trimethyl-silane; tert.-butylnitrite In acetonitrile at 50℃; for 1 h; Step 3. Synthesis of 4-chlorofuro[2,3-d]pyrimidine (C3). A mixture of C2 (660 mg, 4.88 mmol), terf-butyl nitrite (12.1 mL, 97.7 mmol), and trimethylsilyl chloride (3.12 mL, 24.4 mmol) in acetonitrile (20 mL) was stirred at 50 °C for 1 hour. The reaction was cooled to room temperature and quenched with aqueous sodium hydroxide solution (2 M, 30 mL). The aqueous layer was extracted with ethyl acetate (3 x 50 mL), and the combined organic layers were dried over sodium sulfate. The solvent was removed in vacuo and the residue was purified via chromatography on silica gel (Gradient: 0percent to 30percent ethyl acetate in heptane) to provide the product as a volatile white solid. Yield: 168 mg, 1.09 mmol, 22percent. LCMS m/z 154.8 [M+H]+. 1 H NMR (400 MHz, CDCI3) δ 8.77 (s, 1 H), 7.76 (d, J=0.8 Hz, 1 H), 7.25 (d, J=0.8 Hz, 1 H).
References: [1] Journal of the American Chemical Society, 2006, vol. 128, # 48, p. 15372 - 15373.
[2] Patent: WO2007/38387, 2007, A2, . Location in patent: Page/Page column 80-81.
[3] Patent: WO2015/162518, 2015, A1, . Location in patent: Page/Page column 108.
 

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