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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Synonyms: 6-Amino-1,3-dimethyluracil
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 6642-31-5 |
Formula : | C6H9N3O2 |
M.W : | 155.15 |
SMILES Code : | O=C1N(C)C(C=C(N)N1C)=O |
Synonyms : |
6-Amino-1,3-dimethyluracil
|
MDL No. : | MFCD00006552 |
InChI Key : | VFGRNTYELNYSKJ-UHFFFAOYSA-N |
Pubchem ID : | 81152 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.16 g; > 95% | General procedure: To 6.6 g (13 mmol) of 1 in 30 ml of MeCN were added 5.4 g (39 mmol) of K2CO3 and 26 mmol of the nucleophile 2a (8.4 g), 2b (9.0 g), 2c (7.2 g), 2d (5.18 g) 2e (6.01 g), 2f (5.5 g), 2g (5.67 g), 2h (5.67 g), 2i (4.58 g), 2j (6.63 g), 2k (5.05 g), 2l (3.28 g), 2m (8.54 g), 2n (5.31 g). The reaction mixture was stirred at room temperature or at 50 C (in case of 2a, 2g, 2h, 2m, and 2n) under an argon atmosphere. The course of the reaction was monitored by TCL (SiO2, CH3COCH3/CHCl3, 1:3) by following the disappearance of the initial complexes 1. Upon completion of the reaction, the mixture was filtered and extracted by CHCl3 (3 × 50 ml). A small part of the mixture (0.5 g) was separated by column chromatography (20 × 30 cm, SiO2, CH3Cl/CH3COCH3 (5:1)) and the structure and absolute configuration of the pure major diastereomer of complexes 3a-n were established by spectroscopic methods. 4.3. Isolation of the target amino acids 4a-n. Decomposition of the diastereomeric complexes 3a-k and isolation of the target beta-substituted alpha-amino acids 4a-k were carried out according to the literature.(d) and (e) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With 2-(3-phenylthioureido)ethylprolinamide; In water; for 0.333333h;Reflux; | General procedure: To an equimolar solution of 6-amino-1,3-dimethyluracil(0.155g, 1mmol), aldehyde(1 mmol) and 4-hydroxycoumarin(0.162g, 1mmol) in 1mL of water, 5mol% of thioureacatalyst was added and the solution wasstirred underreflux condition. In about 5min, the product started forming(as evident from TLC). The stirring was continued untilcompletion of the reaction (monitored by TLC). The resultingmixture was cooled to room temperature and the solid that precipitated out of the solution was filtered off, washedwith water and then with ethanol twice to remove any unreactedstarting materials and trace of catalyst present. Thesolid crudeproduct was then dissolved in ethanol and keptovernight to get thepure recrystallized product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With 2-(3-phenylthioureido)ethylprolinamide; In water; for 0.25h;Reflux; | General procedure: To an equimolar solution of 6-amino-1,3-dimethyluracil(0.155g, 1mmol), aldehyde(1 mmol) and 4-hydroxycoumarin(0.162g, 1mmol) in 1mL of water, 5mol% of thioureacatalyst was added and the solution wasstirred underreflux condition. In about 5min, the product started forming(as evident from TLC). The stirring was continued untilcompletion of the reaction (monitored by TLC). The resultingmixture was cooled to room temperature and the solid that precipitated out of the solution was filtered off, washedwith water and then with ethanol twice to remove any unreactedstarting materials and trace of catalyst present. Thesolid crudeproduct was then dissolved in ethanol and keptovernight to get thepure recrystallized product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With Amberlyst-15; In methanol; at 80℃; for 5h; | General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound. |