5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE
5-bromo-N,N-dimethylpyrimidin-2-amine
CAS: 38696-21-8
Molecular Formula: C6H8BrN3
5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE - Names and Identifiers
| Name | 5-bromo-N,N-dimethylpyrimidin-2-amine |
| Synonyms | 5-Bromo-2-(dimethylamino)pyrimidine 5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE (5-BROMOPYRIMIDIN-2-YL)DIMETHYLAMINE 5-bromo-N,N-dimethylpyrimidin-2-amine 5-Bromo-N,N-dimethylpyrimidin-2-amine 2-broMo-N,N-diMethylpyriMidin-4-aMine 5-Bromo-N,N-dimethyl-2-pyrimidinamine 2-Pyrimidinamine, 5-bromo-N,N-dimethyl- |
| CAS | 38696-21-8 |
| EINECS | 622-734-6 |
| InChI | InChI=1/C6H8BrN3/c1-10(2)6-8-3-5(7)4-9-6/h3-4H,1-2H3 |
5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE - Physico-chemical Properties
| Molecular Formula | C6H8BrN3 |
| Molar Mass | 202.05 |
| Density | 1.553±0.06 g/cm3(Predicted) |
| Melting Point | 74-81°C |
| Boling Point | 272.0±32.0 °C(Predicted) |
| Flash Point | 118.277°C |
| Vapor Presure | 0.006mmHg at 25°C |
| pKa | 2.21±0.10(Predicted) |
| Storage Condition | 2-8°C(protect from light) |
| Refractive Index | 1.599 |
| MDL | MFCD07368228 |
5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. |
| WGK Germany | 3 |
| Hazard Note | Irritant |
5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE - Reference Information
| Uses | 5-bromo-2-(dimethylamino) pyrimidine is a common pharmaceutical and chemical intermediate. Pyrimidine is an important active molecular structure, which has attracted people's attention as a basic block for molecular design and synthesis of new drugs. Studies have shown that different substitution modifications on the pyrimidine ring will significantly affect its physiological activity. For example, 2,4-diaminopyrimidine derivatives have good protein tyrosine phosphatase 1B inhibitory activity; 2-amino-4 alkoxypyrimidine derivatives have biological activity to inhibit cyclin-dependent kinases; pyrimidine thiourea compounds have neuraminidase inhibitory activity and so on. The active compounds reported in the above literature all contain the structure of 2-substituted aminopyrimidine. |
| Preparation | Using 2-aminopyrimidine as raw material, after liquid bromine bromination and further derivatization, the compound 5-bromo-2-aminopyrimidine was obtained, and then methylated The reaction prepares 5-bromo-2-(dimethylamino) pyrimidine. The synthesis reaction formula is shown in Figure 1. Fig. 1 5-bromo-2-(dimethylamino) pyrimidine synthesis reaction formula 2-amino pyrimidine is dissolved in glacial acetic acid, bromine is added dropwise under stirring at room temperature, and the reaction is carried out at room temperature for 1h. After the reaction, the solution was treated with saturated sodium bicarbonate solution until the pH value of the reaction solution was 7-8, then extracted with dichloromethane (50 mLx3), combined with organic layers, dried with anhydrous sodium sulfate, and separated by column chromatography to obtain the compound 5-bromo-2-aminopyrimidine. Bromination of 2-aminopyrimidine is a key step in the reaction. Experiments have found that whether NBS or pure bromine is used as the brominating reagent, bromination first occurs at the 5th position on the pyrimidine ring. The reason may be due to the presence of amino groups, which makes the reaction proceed through the electrophilic substitution reaction mechanism. In addition, products with different bromination levels can be obtained by controlling the reaction dosage of pure bromine. In the further derivatization of 2-amino -5-bromopyrimidine, the polar solvent DMSO was used and the reaction was accelerated by ultrasound. The N,N-dimethylformamide solution is stirred for 30 minutes, methyl iodide is slowly added dropwise at 0 ℃, the dropwise is completed, and the temperature is raised to room temperature for reaction. TLC detects the progress of the reaction. After the reaction is complete, ethyl acetate is added, washed 3 to 4 times, the organic phase is dried with anhydrous magnesium sulfate, filtered, and concentrated to obtain the product, namely 5-bromo-2-(dimethylamino) pyrimidine. |
Last Update：2024-04-09 21:01:54
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View History
5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE
Cyclopentanone, 2,2-dimethyl-3-(1-methylethyl)-, oxime, (1E,3R)- (9CI)
1H-Pyrazole-4-carboxaldehyde, 1-propyl- (9CI)
N-叔丁氧羰基-6 -氨基-3-氯-2-氟苯甲酸
Benzo[1,3]dioxol-5-ylMethyl-piperidin-4-yl-aMine hydrochloride
Phosphonic acid, [(9-oxo-9H-xanthen-1-yl)methyl]-, diethyl ester (9CI)
N-{[5-(4-bromophenyl)furan-2-yl]methyl}-3-[(1-methyl-1H-tetrazol-5-yl)sulfanyl]propan-1-amine
2-Trimethylsilyloxybenzoic acid trimethylsilyl ester
3-(3-氟吡啶-2-基)丙烯酸乙酯
2(1H)-Pyridinone, 1-(1-methylethyl)-
Cyclopentanone, 2,2-dimethyl-3-(1-methylethyl)-, oxime, (1E,3R)- (9CI)
1H-Pyrazole-4-carboxaldehyde, 1-propyl- (9CI)
N-叔丁氧羰基-6 -氨基-3-氯-2-氟苯甲酸
Benzo[1,3]dioxol-5-ylMethyl-piperidin-4-yl-aMine hydrochloride
Phosphonic acid, [(9-oxo-9H-xanthen-1-yl)methyl]-, diethyl ester (9CI)
N-{[5-(4-bromophenyl)furan-2-yl]methyl}-3-[(1-methyl-1H-tetrazol-5-yl)sulfanyl]propan-1-amine
2-Trimethylsilyloxybenzoic acid trimethylsilyl ester
3-(3-氟吡啶-2-基)丙烯酸乙酯
2(1H)-Pyridinone, 1-(1-methylethyl)-