2,6-Dimethoxy-4-pyrimidinamine
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2,6-Dimethoxy-4-pyrimidinamine
structure -
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CAS No:
3289-50-7
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Formula:
C6H9N3O2
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Chemical Name:
2,6-Dimethoxy-4-pyrimidinamine
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Synonyms:
4-Pyrimidinamine,2,6-dimethoxy-;Pyrimidine,4-amino-2,6-dimethoxy-;2,6-Dimethoxy-4-pyrimidinamine;2,6-Dimethoxy-4-aminopyrimidine;4-Amino-2,6-dimethoxypyrimidine;NSC 166290;(2,6-Dimethoxypyrimidin-4-yl)amine
- Categories:
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CAS No:
2,6-Dimethoxy-4-pyrimidinamine Basic Attributes
155.15
155.15
221-946-2
LSF4SEX5LP
166290
DTXSID2062959
2933599090
Characteristics
70.3
0.5
White Crystalline
1.2±0.1 g/cm3
110-140 °C
340.1ºC at 760 mmHg
159.5±28.7 °C
1.547
methanol: soluble 25mg/mL, clear, colorless to yellow
Safety Information
IRRITANT
NONH for all modes of transport
3
36/37/38
26-37/39
Xi
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 102 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2,6-Dimethoxy-4-pyrimidinamine Use and Manufacturing
General procedure: Synthesis of Aromatic Amines Copper iodide (0.05 mmol), ligand L-II-71 (0.05 or 0.1 mmol), potassium phosphate (1.1 mmol) were added into a 10 mL of Schlenk tube. The tube was then evacuated and backfilled with argon (this sequence was repeated three times), and then aryl chloride (1.0 mmol), 1 mL of DMSO and ammonium hydroxide (2.0 mmol) were added. The reaction mixture was well stirred at 110C. or 120C. for 24 hours. After cooling, water and ethyl acetate were added and mixture was separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic phase was dried over anhydrous sodium sulfate. After concentration, the residue was purified by column chromatography to give the product aromatic amines.10 mmol (1.55 g) of the pale yellow powder obtained in the step (2) was added to a sodium methoxide methanol solution (sodium methoxide content: 25 wt%) containing 15 mmol of sodium methoxide, and then refluxed at 60 C for 3 h. After the heat preservation, the distillation temperature is controlled to 80 C, the methanol is steamed at normal pressure, and the vacuum is distilled to a negative pressure of -0.07 MPa until no distillate is obtained. After distillation, the acetone is added.Equal mass of water, then add sodium carbonate to adjust the pH to 9, cool down to 10 C, filtered, washed with water, and dried to give a pale yellow powder of 4-amino-2, 6-dimethoxypyrimidine 1.33 g, total yield It is 86% (based on methyl cyanoacetate).200 g of methanol and 30 g of solid sodium hydroxide were added to a 500 ml four-necked flask, stirred and dissolved, and 58 g of 2-chloro-4-amino-6-methoxypyrimidine was added thereto, and the temperature was raised to 60. C, heat preservation for 5 hours, the end of the heat preservation, under vacuum conditions, methanol is distilled off below 50 C, the distillation is finished, water is added to the bottle, stirred and cooled to below 10 C, kept for 1 hour, suction filtered, and the filter cake is washed with water and filtered. The cake was dried at 55 C for 10 hours to give 46.5 g of 4-amino-2, 6-dimethoxypyrimidine in a total yield of 60%.The 500 ml frame stirred reactor was evacuated three times with nitrogen.Remove the air and moisture inside, 108.04 g of solid sodium methoxide and 120.12 g of urea were added under nitrogen.Stir until evenly mixed, Then, 198.18 g of methyl cyanoacetate was added dropwise under nitrogen protection.The reaction was continued at 105 C for 7 hours.At the end of the reaction, the methanol produced by the reaction is distilled off under reduced pressure.The solid was released to give 338.05 g of the sodium salt of 4-amino-2, 6-dihydroxypyrimidine.The yield was 98.80%. 450g of methanol was added to the 1L reaction flask.100 g of sodium salt of 4-amino-2, 6-dihydroxypyrimidine, The temperature control does not exceed 50 C into the 168.43g methyl iodide, At the end of the feeding, the reaction was kept at 65 C for 8 hours.The mixture was cooled to room temperature, filtered, and the filtrate was concentrated to recover about 350 g of methanol. The concentrated liquid was cooled and crystallized, filtered, and the filter cake was washed with a little methanol and filtered.Drying 88.38g 4-amino-2, 6-dimethoxypyrimidine, The yield was 97.51%.
Used as pharmaceutical intermediate
4-Pyrimidinamine, 2,6-dimethoxy-: INACTIVE
Computed Properties
Molecular Weight:155.15
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:155.069476538
Monoisotopic Mass:155.069476538
Topological Polar Surface Area:70.3
Heavy Atom Count:11
Complexity:122
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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