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Chemistry
Organic Building Blocks
Amines
2-Aminothieno[2,3-d]pyrimidin-4(3H)-one
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[ CAS No. 1010068-13-9 ] {[proInfo.proName]}

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Chemical Structure| 1010068-13-9
Chemical Structure| 1010068-13-9
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CAS No. :1010068-13-9 MDL No. :
Formula : C6H5N3OS Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 167.19 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 1010068-13-9 ]

* 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 [ 1010068-13-9 ]

[ 1010068-13-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 4651-81-4 ]
  • [ 29671-92-9 ]
  • [ 1010068-13-9 ]
YieldReaction ConditionsOperation in experiment
47% Synthesis of compound 2 (2-aminothienor2,3-dipyrimidin-4-ol)To a solution of cyanamide (1.26 g, 30.0 mmol) in dioxane (10.0 ml_) was added 4N HCI in dioxane (10.0 mL, 40.0 mmol) dropwise. The resulting chloroformamidine (compound 1) precipitated and was stirred for 1 hour, then the solvent was removed under vacuum. The chloroformamidine (compound 1) was partially dissolved in diglyme (20.0 mL) and methyl 2-aminothiophene-3-carboxylate (1.89 g, 12.0 mmol) was added in one portion. This suspension was heated to reflux (2000C oil bath) until all solids dissolved as a pink-brown color solution (-10 minutes). The reaction mixture was then cooled to room temperature, and the precipitate was collected by filtration. The crude material was redisolved in hot (7O0C) 2N NaOH (50 mL), cooled to room temperature, neutralized with concentrated HCI to pH 2.3 and the precipitate collected by filtration to afford 941 mg of 2-aminothieno[2,3-d]pyrimidin-4-o! (compound 2) as a sand color solid (47% yield). 1H NMR (400 MHz, DMSOd6) ? ppm 6.53 (s, 2 H) 6.96 (d, J=5.81 Hz, 1 H) 7.08 (d, J=5.81 Hz, 1 H) 10.90 (s, 1 H).
Reference： [1]Patent: WO2008/59368,2008,A2 .Location in patent: Page/Page column 41-42
  • 2
  • [ 1010068-13-9 ]
  • [ 1538-75-6 ]
  • [ 1028332-09-3 ]
YieldReaction ConditionsOperation in experiment
61% With dmap; triethylamine In N,N-dimethyl-formamide at 80℃; for 16h; GA.3 Synthesis of compound 3 (N-(4-hvdroxythienor2,3-d1pyrimidin-2-yl)-2,2- dimethylpropanamide) A reaction mixture of 2-aminothieno[2,3-d]pyrimidin-4-ol (compound 2, 941 mg, 5.63 mmol), trimethylacetic anhydride/Piv2O (2.3 mL, 1 1.3 mmol), triethylamine (1.6 mL, 11.3 mmol) and DMAP (138 mg, 1.13 mmol) in 4mL of DMF was stirred at 8O0C for 16 hours. The reaction mixture was partitioned between EtOAc (500 mL) and saturated NaHCO3 (100 mL) and brine (100 mL). The combined organic layers were dried (Na2SO4) and then concentrated by vacuum. The residue was purified by Biotage system (4OM, EtOAc:hexane /0% to 30%) to collect the desired fractions of 861 mg of N-(4- hydroxythieno[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamide (compound 3) as a white solid (61% yield). 1H NMR (400 MHz, chloroform-D) ? ppm 1.32 (s, 9 H) 7.07 (d, J=5.81 Hz, 1 H) 7.41 (d, J=5.81 Hz, 1 H) 8.08 (s, 1 H).
Reference： [1]Current Patent Assignee: PFIZER INC - WO2008/59368, 2008, A2 Location in patent: Page/Page column 42
  • 3
  • [ 29671-92-9 ]
  • [ 31891-06-2 ]
  • [ 1010068-13-9 ]
YieldReaction ConditionsOperation in experiment
71% With dimethylsulfone; at 130℃; for 0.5h; Example 349 Synthesis of 2-amino-thieno[2,3-d]pyrimidin-4-(3H)-one A suspension of <strong>[31891-06-2]ethyl 2-amino-thiophene-3-carboxylate</strong> (0.4 g, 2.34 mmol), chloroformamidine hydrochloride (0.67 g, 5.84 mmol) and dimethylsulfone (0.53 g, 11.7 mmol) was heated at 130 C. for 30 minutes. After cooling down to room temperature, water (10 ml) was added and ammonium hydroxide was used to neutralize the suspension till pH=8. The solid was filtered off, washed with water and dried, yielding the crude title compound (71%, 277 mg). The crude residue was used as such for further reaction. MS m/z (%): 168 ([M+H]+, 100)
45% With dimethylsulfone; at 120 - 130℃; for 0.5h; A mixture of <strong>[31891-06-2]ethyl 2-aminothiophene-3-carboxylate</strong> (0.5 g, 3.18 mmol), chloroformamidine hydrochloride (0.91 g, 7.95 mmol) and dimethylsulfone (1.50 g, 15.9 mmol) was heated at 120-130 C. for 30 minutes. After cooling down to room temperature, water (10 ml) was added and ammonium hydroxide was used to neutralize the suspension. The solid was filtered off, washed with water and dried. The crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 10:1) to yield the title compound as a white solid (0.24 g, 45%).1H NMR (300 MHz, DMSO, 25 C.): delta=10.89 (s, 1H, NH), 7.09 (d, J=5.8 Hz, 1H, CH), 6.97 (d, J=5.8 Hz, 1H, CH), 6.52 (s, 2H, NH2) ppm.HRMS: calcd for C6H6N3OS 168.02316, found 168.02239.
45% With dimethylsulfone; at 120 - 130℃; for 0.5h; Example 306 Synthesis of 2-aminothieno[2,3-d]pyrimidin-4(3H)-one A mixture of <strong>[31891-06-2]ethyl 2-aminothiophene-3-carboxylate</strong> (0.5 g, 3.18 mmol), chloroformamidine hydrochloride (0.91 g, 7.95 mmol) and dimethylsulfone (1.50 g, 15.9 mmol) was heated at 120-130 C. for 30 minutes. After cooling down to room temperature, water (10 ml) was added and ammonium hydroxide was used to neutralize the suspension. The solid was filtered off, washed with water and dried. The crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 10:1) to yield the title compound as a white solid (0.24 g, 45%). 1H NMR (300 MHz, DMSO, 25 C.): delta=10.89 (s, 1H, NH), 7.09 (d, J=5.8 Hz, 1H, CH), 6.97 (d, J=5.8 Hz, 1H, CH), 6.52 (s, 2H, NH2) ppm. HRMS: calcd for C6H6N3OS 168.02316, found 168.02239.
45% With dimethylsulfone; at 120 - 130℃; for 0.5h; Example 306 Synthesis of 2-aminothieno[2,3-d]pyrimidin-4(3H)-one A mixture of <strong>[31891-06-2]ethyl 2-aminothiophene-3-carboxylate</strong> (0.5 g, 3.18 mmol), chloroformamidine hydrochloride (0.91 g, 7.95 mmol) and dimethylsulfone (1.50 g, 15.9 mmol) was heated at 120-130 C. for 30 minutes. After cooling down to room temperature, water (10 ml) was added and ammonium hydroxide was used to neutralize the suspension. The solid was filtered off, washed with water and dried. The crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 10:1) to yield the title compound as a white solid (0.24 g, 45%). 1H NMR (300 MHz, DMSO, 25 C.): delta=10.89 (s, 1H, NH), 7.09 (d, J=5.8 Hz, 1H, CH), 6.97 (d, J=5.8 Hz, 1H, CH), 6.52 (s, 2H, NH2) ppm. HRMS: calcd for C6H6N3OS 168.02316. found 168.02239.

Reference： [1]Patent: US2013/190297,2013,A1 .Location in patent: Paragraph 1315; 1316
[2]Patent: US2012/46278,2012,A1 .Location in patent: Page/Page column 81
[3]Patent: US2013/190297,2013,A1 .Location in patent: Paragraph 1210; 1211; 1212
[4]Patent: US2014/88088,2014,A1 .Location in patent: Paragraph 1225-1227

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