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Chemical Structure| 2434-53-9 Chemical Structure| 2434-53-9
Chemical Structure| 2434-53-9

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6-Amino-1-methyluracil is an organic compound with potential biological activity.

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Product Details of 6-Amino-1-methyluracil

CAS No. :2434-53-9
Formula : C5H7N3O2
M.W : 141.13
SMILES Code : O=C1NC(C=C(N)N1C)=O
MDL No. :MFCD00075366
InChI Key :GZLZRPNUDBIQBM-UHFFFAOYSA-N
Pubchem ID :75520

Safety of 6-Amino-1-methyluracil

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 6-Amino-1-methyluracil

* 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.

  • Downstream synthetic route of [ 2434-53-9 ]

[ 2434-53-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 2434-53-9 ]
  • (R)-1-(5-Hydroxy xyl)-7-benzyl-3,8-dimethylxanthin [ No CAS ]
  • [ 6972-82-3 ]
YieldReaction ConditionsOperation in experiment
With sodium nitrite; In water; acetic acid; Example 4 Synthesis of (R)-1-(5-Hydroxy xyl)-7-benzyl-3,8-dimethylxanthin (CT12407) Glacial acetic acid (4.5 ml, 75 mmol) was added to a suspension of 6-amino-1-methyluracil (5.66 g, 50 mmol) in hot (100 ml). Sodium nitrite (4.14 g) was added in portions and the reaction mixture was stirred for 1 hour. The precipitate was collected by filtration, washed with water (75 ml) and then suspended in water (100 ml). The mixture was warmed to 50° C. and sodium dithionite (10 g) was added in portions keeping the temperature of the reaction between 50-55° C. The mixture was stirred at 50° C. for 1 hr and then cooled to room temperature and filtered. The solid was washed with water (2*25 ml), acetone (2*25 ml) and dried under vacuum to provide 5,6-diamino-1-methyluracil (5.6 g).
  • 2
  • [ 2434-53-9 ]
  • [ 6972-82-3 ]
YieldReaction ConditionsOperation in experiment
93% With hydrogenchloride; sodium nitrite; In water; at 0 - 25℃; for 2h; 6-Amino-1-methylpyrimidine-2,4-dione (10.0 g, 70.1 mmol) was dissolved in water (100 mL). Hydrochloric acid (7 mL, 84.0 mmol, 12 N) was added dropwise at 0C while stirring. Then sodium nitrite (5.80 g, 84.2 mmol) was dissolved in water (50 mL) and added dropwise to the reaction solution to give a purple precipitate. The reaction was stirred at 25C for 2 hours, filtered and washed with cold water to give a purple solid. The solid was dissolved in water (100 mL) and sodium hydrosulphite (18.7 g, 118 mmol) was added in batches while stirring, heated to 60C and stirred for 0.5 h, cooled to 25C and stirred for 16 h, filtered, washed with cold water (50 mL), ethanol (50 mL), acetone (50 mL) respectively, and dried to give 5,6-diamino-1-methylpyrimidine-2,4-dione (8.60 g, as a pale yellow solid) with a yield of 93%. 1H NMR (400 MHz, DMSO-d6) delta 10.49(br, 1H), 6.15(br, 2H), 3.25(s, 3H), 2.95(br, 2H). MS-ESI calcd. [M + H]+ 157, found 157.
93% With hydrogenchloride; sodium nitrite; In water; at 0 - 25℃; for 2h; 6-Amino-1-methylpyrimidin-2,4-dione (10.0 g, 70.1 mmol) was dissolved in water (100 mL), and then hydrochloric acid (7 mL, 84.0 mmol, 12N) was added dropwise at 0 C. while stirring. Sodium nitrite (5.80 g, 84.2 mmol) was dissolved in water (50 mL), which was added dropwise into the reactants, then a purple precipitate appeared. The reaction solution was stirred 25 C. for 2 hours, the then was filtered. The filtrate was washed with cold water to give a purple solid. The solid was dissolved in water (100 mL), and then sodium hypodisulfite (18.7 g, 118 mmol) was added in batches while stirring. The reaction solution was heated to 60 C. and stirred for 0.5 hour, and then was cooled to 25 C. and stirred for 16 hours. The reaction solution was filtered and the filtrate was washed with water (50 mL), ethanol (50 mL) and propanone (50 mL), respectively, followed by drying to give a product 5,6-diamino-1-methylpyrimidin-2,4-dione (8.60 g, pale yellow solid), with a yield of 93%. 1H NMR (400 MHz, DMSO-d6) delta10.49 (s, 1H), 6.15 (s, 2H), 3.25 (s, 3H), 2.95 (s, 2H). MS-ESI calculated value: [M+H]+ 157; measured value: 157.
78% With ammonium hydroxide; sodium dithionite; at 50℃; for 1h; The purple solid (3 g, 17.6 mmol) and 25% aqueous ammonia (30 ml) were added to a 100 ml reaction flask, and sodium dithionite (10.8 g, 61.6 mmol) was added in portions and stirred at 50 C for 1 h, and the reaction solution was cooled to room temperature. The reaction was stirred at room temperature for 8 h, filtered, and the filter cake was washed with ice water (10 ml) and icedLight yellow solid (2.15g, 78%)
With sodium nitrite; In water; acetic acid; Example 4 Synthesis of (R)-1-(5-Hydroxyhexyl)-7-benzyl-3,8-dimethylxanthine (CT12407) Glacial acetic acid (4.5 ml, 75 mmol) was added to a suspension of 6-amino-1-methyluracil (5.66 g, 50 mmol) in hot water (100 ml). Sodium nitrite (4.14 g) was added in portions and the reaction mixture was stirred for 1 hour. The precipitate was collected by filtration, washed with water (75 ml) and then suspended in water (100 ml). The mixture was warmed to 50 C. and sodium dithionite (10 g) was added in portions keeping the temperature of the reaction between 50-55 C. The mixture was stirred at 50 C. for 1 hr and then cooled to room temperature and filtered. The solid was washed with water (2*25 ml), acetone (2*25 ml) and dried under vacuum to provide 5,6-diamino-1-methyluracil (5.6 g).
With sodium nitrite; In water; acetic acid; A. Preparation of 5,6-Diamino-1-methyluracil Glacial acetic acid (4.5 ml 75 mmol) was added to a suspension of 6-amino-1-methyluracil (5.66 g, 50 mmol) in hot water (100 ml). Sodium nitrite (4.14 g) was added in portions and the reaction mixture was stirred for 1 hour. The resulting solid was collected by filtration, washed with water (75 ml) and resuspended in water (100 ml).
With sodium nitrite; In water; acetic acid; Example 4 Synthesis of (R)-1-(5-Hydroxyhexyl)-7-benzyl-3,8-dimethylxanthine (CT12407) Glacial acetic acid (4.5 ml, 75 mmol) was added to a suspension of 6-amino-1-methyluracil (5.66 g, 50 mmol) in hot water (100 ml). Sodium nitrite (4.14 g) was added in portions and the reaction mixture was stirred for 1 hour. The precipitate was collected by filtration, washed with water (75 ml) and then suspended in water (100 ml). The mixture was warmed to 50 C. and sodium dithionite (10 g) was added in portions keeping the temperature of the reaction between 50-55 C. The mixture was stirred at 50 C. for 1 hr and then cooled to room temperature and filtered. The solid was washed with water (2*25 ml), acetone (2*25 ml) and dried under vacuum to provide 5,6-diamino-1-methyluracil (5.6 g).

 

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