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CAS No. :175137-13-0 MDL No. :MFCD00205194
Formula : C7H6N2OS Boiling Point : -
Linear Structure Formula :- InChI Key :KJTYNZWEAIRZHT-UHFFFAOYSA-N
M.W : 166.20 Pubchem ID :135439636
Synonyms :

Safety of [ 175137-13-0 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 175137-13-0 ]

* 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 [ 175137-13-0 ]
  • Downstream synthetic route of [ 175137-13-0 ]

[ 175137-13-0 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 175137-13-0 ]
  • [ 175137-21-0 ]
YieldReaction ConditionsOperation in experiment
95% for 2 h; Heating / reflux 4-Chloro-7-methylthieno[3,2-d]pyrimidine (168): A solution of 7-methyl-3H-thieno[3,2-d]pyrimid-4-one (167, 10.6 g, 64.0 mmol) in phosphorus oxychloride (42 mL) was refluxed under N2 for 2 hours. The resulting solution was allowed to cool to room temperature and then neutralized by carefully pouring into a saturated aqueous solution of sodium carbonate (300 mL). The aqueous mixture was extracted with ethyl acetate and the organic layer washed with water and brine, before drying over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue dried over P2O5 under vacuum overnight (11.2 g, 95percent yield, white solid).
81% With trichlorophosphate In N,N-dimethyl-formamide at 110℃; for 4 h; 7-methyl-3H-thieno[3,2-d]pyrimidin-4-one (9 g, 54.2 mmol), DMF (lmL), POCl3 (80mL) were mixed and refluxed for 4 hours at 110°C. The reaction solution was cooled to room temperature, and the reaction mixture was concentrated under reduced pressure. The reaction mixture was added with toluene, and further concentrated under reduced pressure. The resulting residue was neutralized with sodium bicarbonate, subjected to extraction with ethyl acetate, dried, and filtered to obtain the title compound (8.1 g, 81percent). -NMR Spectrum (300 MHz, CDC13): δ 9.01 (s, IH), 7.69 (s, IH), 2.53 (s, 3H)
81% at 110℃; for 4 h; 7-methyl-3H-thieno[3,2-d]pyrimidin-4-one (9 g, 54.2 mmol), DMF (1 mL), POCl3 (80 mL) were mixed and refluxed for 4 hours at 110° C. The reaction solution was cooled to room temperature, and the reaction mixture was concentrated under reduced pressure. The reaction mixture was added with toluene, and further concentrated under reduced pressure. The resulting residue was neutralized with sodium bicarbonate, subjected to extraction with ethyl acetate, dried, and filtered to obtain the title compound (8.1 g, 81percent). 1H-NMR Spectrum (300 MHz, CDCl3): δ 9.01 (s, 1H), 7.69 (s, 1H), 2.53 (s, 3H)
20% for 3 h; Reflux Synthesis of intermediate XI 11-011-07 XIII-01A mixture of Intermediate 1-07 (4.85 g, 24.34 mnmol) and POCI3 (20 mL) was refluxed for 3 h. On cooling, the solvents were removed in vacuo, the residue was suspended in water and the suspension was cooled to 0 °C. Aqueous saturated Na2C03 was added dropwise at 0 °C up to pH~8. The resulting solid was filtered, washed with water and dried to give Intermediate XIII-01 (1.1 g, 20percent) as a white solid. H NMR (300 MHz, DMSO) δ 9.01 (s, 1H), 8.19 (q, J = 1.1 Hz, 1H), 2.39 (d, J = 1.1 Hz, 3H).
1.9 g at 100℃; for 6 h; Commercially available methyl 3-amino-4-methylthiophene-2-carboxylate 13 (16.5 g, 96.0 mmol) was dissolved in formamide (100 mL) and stirred at 150 °C under nitrogen atmosphere. After the starting material consumption had been confirmed by LC-MS, the reaction mixture was cooled to room temperature and then H2O (500 mL) was added to the mixture. The suspension was filtered to collect a white solid that was dried by an oil pump to give 7-methylthieno[3,2-d]pyrimidin-4(3H)-one (12.2 g). The solid was used for the next reaction without further purification. The aforementioned 7-methylthieno[3,2-d]pyrimidin-4(3H)-one (1.85 g) was treated with POCl3 (8.80 mL) and stirred at 100 °C for 6 h. The reaction mixture was cooled to 0 °C, poured into ice-water/ethyl acetate, and extracted with ethyl acetate twice. The organic layer was washed with brine, dried over Na2SO4, and filtered. The organic solvent was concentrated under reduced pressure to give a crude residue. Water (200 mL) was added to the residue and the mixture cooled at 5 °C in the refrigerator for a day. The suspension was filtered to afford 14 (1.90 g, 2 steps 72percent) as a white solid. 1H NMR (400 MHz, DMSO-D6) δ: 9.07 (1H, s), 8.25 (1H, d, J = 1.2 Hz), 2.45 (3H, d, J = 1.2 Hz). 13C NMR (100 MHz, DMSO-D6) δ: 160.7, 153.9, 153.6, 133.9, 133.2, 130.0, 12.5. HRMS (ESI-TOF) m/z: [M+H]+ Calcd for C7H6ClN2S 184.9940; Found 184.9937.

Reference: [1] Patent: US2006/4002, 2006, A1, . Location in patent: Page/Page column 12; 21; 23; 30; 31-32
[2] Patent: WO2013/100632, 2013, A1, . Location in patent: Page/Page column 62
[3] Patent: US2014/371219, 2014, A1, . Location in patent: Paragraph 0436; 0437
[4] Patent: WO2012/156756, 2012, A2, . Location in patent: Page/Page column 99
[5] Patent: WO2011/93684, 2011, A2, . Location in patent: Page/Page column 33; 34
[6] Patent: WO2011/93672, 2011, A2, . Location in patent: Page/Page column 45; 46
[7] Patent: US2012/15962, 2012, A1, . Location in patent: Page/Page column 66
[8] Patent: US2012/302567, 2012, A1, . Location in patent: Page/Page column 20
[9] Patent: US2013/53370, 2013, A1, . Location in patent: Paragraph 0269-0271
[10] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4206 - 4217
  • 2
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  • [ 175137-21-0 ]
YieldReaction ConditionsOperation in experiment
96% With sodium hydrogencarbonate In trichlorophosphate A solution of 7-methyl-3H-thieno[3,2-d]pyrimid-4-one (3, 2.9 g, 18 mmol) in phosphorus oxychloride (18 mL) under N2 was heated at reflux for 1 hour.
The resulting solution was allowed to cool to room temperature and then poured into a saturated aqueous solution of sodium bicarbonate to neutralize.
The aqueous mixture was extracted with diethyl ether.
The organic layer was washed with water followed by saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and the solvent evaporated under reduced pressure to yield 4-chloro-7-methylthieno[3,2-d]pyrimidine (3.1 g, 96percent yield) as a white solid.
Reference: [1] Patent: US6503914, 2003, B1,
  • 3
  • [ 443762-03-6 ]
  • [ 175137-13-0 ]
  • [ 175137-21-0 ]
YieldReaction ConditionsOperation in experiment
84% With ammonium formate In formamide To a solution of ammonium formate (5.1 g, 81 mmol) in formamide (25 mL) at 150° C. was added 3-(formylamino)-4-methyl-2-thiophenecarboxylic acid methyl ester (2, 5.0 g, 25 mmol) as a solid in small portions.
The resulting solution was heated at 150° C. for 5 hours and then allowed to stand at room temperature for 12 hours.
The precipitate that formed was collected by vacuum filtration to give 7-methyl-3H-thieno[3,2-d]pyrimid-4-one (3.4 g, 84percent yield) as white needles.
4-Chloro-7-methylthieno[3,2-d]pyrimidine (4).
Reference: [1] Patent: US6503914, 2003, B1,
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