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CAS No. : | 2055-46-1 | MDL No. : | MFCD00060526 |
Formula : | C4H8N2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NVHNGVXBCWYLFA-UHFFFAOYSA-N |
M.W : | 116.18 | Pubchem ID : | 2723785 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In N,N-dimethyl-formamide; at 120℃; for 3h; | General procedure: A mixture of cyclic thiourea 4a-e (1 mmol) and di(methylsulfanyl)methylenemalononitrile 5a (0.170 g, 1 mmol) in DMF (3 mL) was stirred at 120 C. Upon completion (3 h monitored by TLC), the solvent was removed by rotary evaporator under vacuum. The afforded orange solid washed by ethyl acetate and dried to give 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | To a solution of the corresponding cyclic thiourea1 (1 mmol) in DMF (1.0 mL) was added 2-di(methylsulfanyl) methylene malononitrile 2 (0.170g, 1 mmol). The reaction mixture was stirred for 3 h at120 ±C. Afterward, a solution of dialkyl acetylenedicarboxylates3 (1 mmol) in EtOH (2.0 mL) was addeddropwise to the reaction mixture at room temperature.After completing the addition, the stirring continuedfor another 20 min. Then, the correspondingN-nucleophiles 4 (1.2 eq) were added to the mixture.After stirring for 1 h at room temperature, thesolvent was evaporated by a rotary evaporator andthe residue was washed by EtOH to yield the desiredadducts 5a-m.Methyl 8-amino-10-cyano-6-oxo-9-thioxo-1,3,4,6,8,9-hexahydro-2H-pyrido[4,3-d]pyrimido[1,2-a]pyrimidine-7-carboxylate (5a). Yellow powder,m.p 300 ±C, 0.259 g, yield: 78%. IR (KBr)(max,cm1): 3336 and 3295 (NH2 and NH), 2221 (CN), 1746(CO2Me), 1693 (CO), 1614 (CN), 1578 (CC), 1295(CS), 1084 (C-O). Anal. Calcd. for C13H12N6O3S(332.33): C, 46.98; H, 3.64; N, 25.29%. Found C, 46.97;H, 3.64; N, 25.31. 1H NMR (300 MHz, DMSO-d6): 1.95(2H, m, CH2), 3.30-3.34 (2H, m, CH2N), 3.81 (2H, t,3JHH 4.8 Hz, CH2NH), 3.91 (3H, s, CO2Me), 6.55(2H, s, NH2), 9.35 (1H, s, NH). 13C{1H} (75.0 MHz,DMSO-d6): 19.00, 39.33, 40.44, 58.83, 102.74, 102.94,116.99, 147.14, 154.61, 156.57, 158.45, 160.69, 179.73.MS (EI, 70 eV): 332 (M?, 27), 288 (33), 259 (37), 227(48), 190 (35), 149 (53), 120 (28), 83 (66), 58 (100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | To a solution of the corresponding cyclic thiourea1 (1 mmol) in DMF (1.0 mL) was added 2-di(methylsulfanyl) methylene malononitrile 2 (0.170g, 1 mmol). The reaction mixture was stirred for 3 h at120 ±C. Afterward, a solution of dialkyl acetylenedicarboxylates3 (1 mmol) in EtOH (2.0 mL) was addeddropwise to the reaction mixture at room temperature.After completing the addition, the stirring continuedfor another 20 min. Then, the correspondingN-nucleophiles 4 (1.2 eq) were added to the mixture.After stirring for 1 h at room temperature, thesolvent was evaporated by a rotary evaporator andthe residue was washed by EtOH to yield the desiredadducts 5a-m.Methyl 8-amino-10-cyano-6-oxo-9-thioxo-1,3,4,6,8,9-hexahydro-2H-pyrido[4,3-d]pyrimido[1,2-a]pyrimidine-7-carboxylate (5a). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | To a solution of the corresponding cyclic thiourea1 (1 mmol) in DMF (1.0 mL) was added 2-di(methylsulfanyl) methylene malononitrile 2 (0.170g, 1 mmol). The reaction mixture was stirred for 3 h at120 ±C. Afterward, a solution of dialkyl acetylenedicarboxylates3 (1 mmol) in EtOH (2.0 mL) was addeddropwise to the reaction mixture at room temperature.After completing the addition, the stirring continuedfor another 20 min. Then, the correspondingN-nucleophiles 4 (1.2 eq) were added to the mixture.After stirring for 1 h at room temperature, thesolvent was evaporated by a rotary evaporator andthe residue was washed by EtOH to yield the desiredadducts 5a-m.Methyl 8-amino-10-cyano-6-oxo-9-thioxo-1,3,4,6,8,9-hexahydro-2H-pyrido[4,3-d]pyrimido[1,2-a]pyrimidine-7-carboxylate (5a). |
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