Name | 5-Azacytosine |
Synonyms | 5-Azocytosine 5-AZACYTOSINE 5-Azacytosine 4-Amino-1,3,5-triazin-2-ol 4-Amino-1,3,5-triazin-2-one 4-AMINO-1,3,5-TRIAZIN-2-ONE 4-AMINO-S-TRIAZIN-2(1H)-ONE 2-AMINO-4-HYDROXY-S-TRIAZINE 1,3,5-triazin-2-ol, 4-amino- 5-triazin-2(1h)-one,4-amino-3 4-Amino-1,3,5-triazin-2(1H)-on 6-Amino-1,3,5-triazin-2(1H)-one 4-Amino-1,3,5-triazin-2(1H)-one 4-AMINO-1,3,5-TRIAZINE-2[1H]-ONE 2-Amino-4-hydroxy-1,3,5-triazine 1,3,5-triazin-2(1H)-one, 4-amino- 1,3,5-Triazin-2(1H)-one, 6-amino- |
CAS | 931-86-2 4040-10-2 |
EINECS | 213-242-9 |
InChI | InChI=1/C3H6N4O/c4-2-5-1-6-3(8)7-2/h1,3,8H,(H3,4,5,6,7) |
InChIKey | MFEFTTYGMZOIKO-UHFFFAOYSA-N |
Molecular Formula | C3H4N4O |
Molar Mass | 112.09 |
Density | 1.86 |
Melting Point | >300 °C (lit.) |
Boling Point | 209.98°C (rough estimate) |
Solubility | Aqueous Base (Slightly, Heated), DMSO (Slightly, Heated) |
Appearance | Crystallization |
Color | White to Off-White |
BRN | 116378 |
pKa | 7.61±0.10(Predicted) |
Storage Condition | Keep in dark place,Inert atmosphere,2-8°C |
Refractive Index | 1.8010 (estimate) |
MDL | MFCD00006033 |
Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
WGK Germany | 3 |
RTECS | XZ2854300 |
HS Code | 29336990 |
Application | 5-azacytosine, also known as 4-amino -1,3, 5-triazin-2-one is the basic raw material for the synthesis of 5-azacytidine drugs. As a synthetic pyrimidine base, 5-azacytidine can be combined with ribose to form 5-azacytidine, it can infiltrate the tumor nucleic acid as a pseudo metabolite, and interfere with the physiological function of tumor cells to produce anti-tumor effect. currently developed therapeutic drugs using 5-azacytidine as raw materials include 5-azacytidine, commercial name Vidaza. And 5-aza-2 '-deoxycytidine, trade name Decitabine. This class of drugs has been demonstrated clinically for myelodysplastic syndromes, myeloid leukemia, sickle cell anemia, and in some solid tumors. |
preparation | put 140 of formic acid into the reaction kettle, turn on the stirring, put 25 of dicyandiamide, the reaction temperature will rise gradually by itself, and the temperature should be controlled below 60 ℃. After the reaction temperature no longer rises, the remaining 75kg of dicyandiamide will be added into the reaction kettle in 4-5 hours, the reaction was stirred at 50-60 ° C. For 4 hours, and then the temperature control measures were stopped. The reaction temperature was slowly increased, and the temperature was raised to 100-110 ° C. For 1 hour. 120 of acetic anhydride is dropped into the reaction kettle, and the temperature is maintained at 100~110 ° C. During The dropping process, and after the dropping is completed, the mixture is stirred at this temperature for 45 minutes; 100 of acetic anhydride was added dropwise again, and after the dropwise addition, the temperature was raised to reflux, and the reaction was maintained at reflux for 2 hours. after the reflux was completed, the temperature was lowered to 60-70 ° C. By stirring, 120 of ethanol was added, and the temperature was further lowered to room temperature. Filter, filter cake into the reaction kettle, add 480 of ethyl acetate and 96kg of ethanol, heated to 65~75 ℃, stirred for 1 hour after the hot filter, filter cake drying, 74kg of 5-azacytosine was obtained, the HPLC purity was 98.9%, the content of impurity 1 was 0.34%, and the content of impurity 2 was 0.06%. |