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Chemical Structure| 35265-80-6

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Product Details of [ 35265-80-6 ]

CAS No. :35265-80-6
Formula : C7H6N2O2S
M.W : 182.20
SMILES Code : O=C1NC(C=C(C)S2)=C2C(N1)=O
MDL No. :MFCD20617597

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Application In Synthesis of [ 35265-80-6 ]

* 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.

  • Downstream synthetic route of [ 35265-80-6 ]

[ 35265-80-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 35265-80-6 ]
  • [ 35265-82-8 ]
YieldReaction ConditionsOperation in experiment
98% With trichlorophosphate; In DMF (N,N-dimethyl-formamide); at 100℃; for 2.0h;Heating / reflux; Phosphorus oxychloride (6.85 g, 44.8 mmol) was added to a DMF (1 mL) solution of 2,4-dihydroxy-6-methylthieno[3,2-d]pyrimidine (2.72 g, 14.9 mmol), followed by heating under reflux at 100C for 2 hours. After completion of the reaction, the reaction liquid was poured into ice-water and precipitated crystals were collected by filtration. After the crystals were dissolved in ethyl acetate, the solution was washed with water and brine and then the solvent was removed by evaporation to obtain 2,4-dichloro-6-methylthieno[3,2-d]pyrimidine (3.21 g, 98%). 1H-NMR (400MHz, CDCl3): 2.73(d, 3H, J=1.2Hz), 7.20(q, 1H, J=1.2Hz). mp: 152-153C
With N,N-dimethyl-aniline; trichlorophosphate; at 20 - 100℃; for 2.0h; (2) To a mixture of 6-methylthieno[3,2-d]pyrimidine-2,4-diol (0.77 g) and phosphorus oxychloride (8 mL) was added N,N-dimethylaniline (1.6 mL) at room temperature, and the mixture was stirred at 100C for 2 h. The reaction solution was added dropwise to water with ice cooling, and the aqueous layer was extracted with chloroform. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (silica gel, chloroform) to obtain 2,4-dichloro-6-methylthieno[3,2-d]pyrimidine (0.50 g). LC/MS: ESI+ (m/z) 219 (M++1) 1H-NMR (300 MHz, CDCl3): delta7.20-7.21 (m, 1H), 2.73 (d, J=1.2 Hz, 3H)
  • 2
  • [ 35265-80-6 ]
  • [ 35265-82-8 ]
YieldReaction ConditionsOperation in experiment
41% With trichlorophosphate; for 10.0h;Heating / reflux; A mixture of 2,4-dihydroxy-6-methyl-thieno[3,2-d]pyrimidine 4c (45.14 g, 0.25 mol) and phosphorus oxychloride (500 ml) was refluxed for 10 h, whereby a clear brown solution was formed. The reaction mixture was cooled to room temperature and the excess of phosphorus oxychloride was evaporated in vacuo. The residue was poured into ice water and the aqueous mixture was extracted with chloroform. The organic phase was separated, washed with water until neutral and dried over magnesium sulfate. The final solution was passed through a silica gel plug. The solvent was evaporated in vacuo to yield 25.37 g of white solid. Recrystallizion from ethanol afforded 4d (22.5 g, 41%) as white needles. 1H NMR (CDCI3, 400 MHz) delta 7.13 (s, 1 H), 2.66 (s, 3H). 13C NMR (CDCI3, 100 MHz) delta 164.55, 156.48, 156.27, 154.62, 129.44, 122.70, 17.74.
 

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