| Identification | Back Directory | [Name]
2-Pyrimidinamine, 4-chloro-5-methyl- (9CI) | [CAS]
20090-58-8 | [Synonyms]
4-Chloro-5-methylpyrimidin-2-amine
4-Chloro-5-methyl-2-pyrimidinamine
2-Amino-4-chloro-5-methylpyrimidine
4-Chloro-2-amino-5-methylpyrimidine
2-Pyrimidinamine, 4-chloro-5-methyl-
2-Pyrimidinamine, 4-chloro-5-methyl- (9CI)
4-Chloro-5-methylpyrimidin-2-amine, 2-Amino-4-chloro-5-methyl-1,3-diazine | [Molecular Formula]
C5H6ClN3 | [MDL Number]
MFCD00725898 | [MOL File]
20090-58-8.mol | [Molecular Weight]
143.57 |
| Chemical Properties | Back Directory | [Melting point ]
184-185℃ | [Boiling point ]
320.8±34.0 °C(Predicted) | [density ]
1.349±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [form ]
solid | [pka]
3.99±0.10(Predicted) | [color ]
Light yellow to yellow |
| Hazard Information | Back Directory | [Synthesis]
Step b: Synthesis of 4-chloro-2-amino-5-methylpyrimidine
5-Methylisocytosine (3 g, 24.0 mmol) was mixed with phosphorus trichloride (POCl3, 20 mL) and heated to reflux for 45 minutes. Upon completion of the reaction, the excess phosphorous trichloride was removed by distillation under reduced pressure. The residue was slowly poured into ice water and the pH was subsequently adjusted to alkaline with ammonia at 10 °C. The precipitated solid was collected by filtration and recrystallized from ethanol to afford the target compound 4-chloro-2-amino-5-methylpyrimidine (1 g, 29.0% yield).
1H NMR (400 MHz, DMSO-d6) δ: 8.11 (s, 1H, pyrimidine ring H), 6.81 (br s, 2H, NH2), 2.04 (s, 3H, CH3). | [References]
[1] Patent: US2009/221597, 2009, A1. Location in patent: Page/Page column 41
[2] Journal of the Chemical Society, 1947, p. 41,45 |
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