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| | 4-Amino-6-chloro-2-(methylthio)pyrimidine Basic information | | Uses |
| | 4-Amino-6-chloro-2-(methylthio)pyrimidine Chemical Properties |
| Melting point | 130-132 °C (lit.) | | Boiling point | 338.7±22.0 °C(Predicted) | | density | 1.395 (estimate) | | refractive index | 1.6100 (estimate) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Methanol | | pka | 1.11±0.10(Predicted) | | form | Crystalline Powder | | color | Off-white to beige or yellow | | InChI | 1S/C5H6ClN3S/c1-10-5-8-3(6)2-4(7)9-5/h2H,1H3,(H2,7,8,9) | | InChIKey | ISUXMAHVLFRZQU-UHFFFAOYSA-N | | SMILES | CSc1nc(N)cc(Cl)n1 | | CAS DataBase Reference | 1005-38-5(CAS DataBase Reference) | | NIST Chemistry Reference | Pyrimidine, 4-amino-6-chloro-2-(methylthio)-(1005-38-5) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 37/39-26 | | WGK Germany | 3 | | HS Code | 29335990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 4-Amino-6-chloro-2-(methylthio)pyrimidine Usage And Synthesis |
| Uses | 4-Amino-6-chloro-2-(methylthio)pyrimidine is a halogenated heterocycle, a useful synthesis intermediate. | | Chemical Properties | off-white to beige or yellow crystalline powder | | Uses | 4-Amino-6-chloro-2-(methylthio)pyrimidine is a halogenated heterocycle, a useful synthesis intermediate. | | Synthesis Reference(s) | Journal of the American Chemical Society, 77, p. 1098, 1955 DOI: 10.1021/ja01610a006 | | Synthesis | General procedure for the synthesis of 4-amino-6-chloro-2-(methylthio)pyrimidine from 4,6-dichloro-2-(methylthio)pyrimidine:
1. 4,6-Dichloro-2-(methylthio)pyrimidine was added slowly in a 2L autoclave with THF and ammonia.
2. The reaction mixture was heated to 50-60°C and kept at that temperature for 3-4 hours (pressure in the reactor was maintained at 7-8 Kg/cm2).
3. The progress of the reaction was monitored by TLC.
4. After completion of the reaction, the reaction mixture was cooled to 25-35°C. 5.
5. Concentrate the reaction mixture under vacuum. 6.
6. Hexane was added and stirred at 25-35 °C for 30-45 min.
7. Collect the solid product by filtration and wash with hexane.
8. Wash the solid product with water (2 x 400 mL).
9. Dry the solid product at 25-35 °C until the moisture content (MC) is less than 2%.
Yield: 352.0 g. Yield: 97.77%.
HPLC purity: 99.07%.
Note: For different analogs, other suitable conditions may be used, such as the use of methanol or dioxane solutions of ammonia.
Example 1-2: Preparation of 4-amino-6-chloro-2-methylthiopyrimidine, step 6.1. | | References | [1] Patent: WO2011/97594, 2011, A2. Location in patent: Page/Page column 100-101
[2] Chemistry - A European Journal, 1999, vol. 5, # 12, p. 3450 - 3458
[3] Patent: WO2007/141571, 2007, A2. Location in patent: Page/Page column 25
[4] American Chemical Journal, 1904, vol. 32, p. 353
[5] Patent: US2005/288502, 2005, A1. Location in patent: Page/Page column 20 |
| | 4-Amino-6-chloro-2-(methylthio)pyrimidine Preparation Products And Raw materials |
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