CAS No. :	6972-82-3
Formula :	C₅H₈N₄O₂
M.W :	156.14
SMILES Code :	CN1C(=O)NC(=O)C(N)=C1N
Synonyms :	5,6-Diamino-1-methyluracil
MDL No. :	MFCD00091924
InChI Key :	PSIJQVXIJHUQPJ-UHFFFAOYSA-N
Pubchem ID :	157184

Safety of 5,6-Diamino-1-methyluracil

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

Application In Synthesis of 5,6-Diamino-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 [ 6972-82-3 ]

[ 6972-82-3 ] Synthesis Path-Downstream 1~54

1
[ 103-82-2 ]
[ 6972-82-3 ]
phenyl-acetic acid-(6-amino-1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylamide) [ No CAS ]

References: [1]Chemicke Zvesti,1956,vol. 10,p. 96,106.
Chem.Abstr.,1956,p. 13 947.

2
[ 50-00-0 ]
[ 6972-82-3 ]
[ 1076-22-8 ]

References: [1]Chemische Berichte,1906,vol. 39,p. 229.

3
[ 64-18-6 ]
[ 6972-82-3 ]
[ 14785-95-6 ]

4
[ 849585-22-4 ]
[ 6972-82-3 ]
8-(1-hydroxy-ethyl)-3-methyl-3,7⁽⁹⁾-dihydro-purine-2,6-dione [ No CAS ]

References: [1]Patent: DE213711, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 9,p. 1010.

5
[ 600-22-6 ]
[ 6972-82-3 ]
[ 2625-22-1 ]

References: [1]Chemische Berichte,1957,vol. 90,p. 2631,2633,2635.

6
[ 6972-82-3 ]
[ 2757-85-9 ]
[ 90350-04-2 ]

References: [1]Chemische Berichte,1957,vol. 90,p. 2631,2633,2635.

7
[ 6972-82-3 ]
[ 420-05-3 ]
[ 605-99-2 ]

References: [1]Justus Liebigs Annalen der Chemie,1923,vol. 432,p. 287.

8
[ 6972-82-3 ]
pentanetrione [ No CAS ]
6-acetyl-1,7-dimethyl-1<i>H</i>-pteridine-2,4-dione [ No CAS ]

References: [1]Chemische Berichte,1908,vol. 41,p. 3964.

9
[ 6972-82-3 ]
[ 631-23-2 ]
[ 100949-42-6 ]

References: [1]Journal of the American Chemical Society,1953,vol. 75,p. 4446,4447.

10
[ 6972-82-3 ]
[ 541-41-3 ]
[ 55441-55-9 ]

References: [1]Chemische Berichte,1900,vol. 33,p. 3047.
Chemisches Zentralblatt,1901,vol. 72,p. 548.

11
[ 6972-82-3 ]
[ 144-62-7 ]
[ 114062-82-7 ]

References: [1]Justus Liebigs Annalen der Chemie,1941,vol. 546,p. 98,100.

12
[ 6972-82-3 ]
[ 144-62-7 ]
(6-amino-1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-oxalamic acid [ No CAS ]

References: [1]Patent: DE213711, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 9,p. 1010.

13
[ 6972-82-3 ]
[ 517-21-5 ]
[ 50256-18-3 ]

References: [1]Chemische Berichte,1957,vol. 90,p. 2631,2633,2635.

14
[ 6972-82-3 ]
[ 100-52-7 ]
[ 19845-24-0 ]

References: [1]Angewandte Chemie,1968,vol. 80,p. 534.

15
[ 6972-82-3 ]
[ 90-02-8 ]
8-(2-hydroxy-phenyl)-3-methyl-3,7-dihydro-purine-2,6-dione [ No CAS ]

References: [1]Chemische Berichte,1906,vol. 39,p. 229.

16
[ 6972-82-3 ]
[ 77287-34-4 ]
[ 1076-22-8 ]

References: [1]Chemische Berichte,1950,vol. 83,p. 201,209.

17
[ 6972-82-3 ]
[ 127-17-3 ]
[ 2625-22-1 ]

References: [1]Chemische Berichte,1908,vol. 41,p. 3964.

18
[ 6972-82-3 ]
[ 372-09-8 ]
[ 861520-49-2 ]

References: [1]Patent: DE213711, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 9,p. 1010.

19
[ 6972-82-3 ]
[ 222851-56-1 ]
[ 62700-61-2 ]

References: [1]Zhurnal Obshchei Khimii,1959,vol. 29,p. 3214,3216; engl. Ausg. S. 3178, 3180.

20
[ 6972-82-3 ]
[ 431-03-8 ]
[ 50256-21-8 ]

References: [1]Journal of Agricultural and Food Chemistry,2016,vol. 64,p. 5079 - 5084.
[2]Chemische Berichte,1908,vol. 41,p. 3964.

21
[ 6972-82-3 ]
[ 79-11-8 ]
chloro-acetic acid-(6-amino-1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylamide) [ No CAS ]

References: [1]Patent: DE209729, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 9,p. 1008.

22
[ 6972-82-3 ]
[ 134-81-6 ]
[ 19845-24-0 ]

References: [1]Biochemische Zeitschrift,1935,vol. 281,p. 206,212.

23
[ 6972-82-3 ]
[ 84-11-7 ]
[ 78270-80-1 ]

References: [1]Biochemische Zeitschrift,1935,vol. 281,p. 206,212.

24
[ 6972-82-3 ]
[ 78-98-8 ]
[ 119248-03-2 ]

References: [1]Chemische Berichte,1956,vol. 89,p. 2904,2908.

25
[ 6972-82-3 ]
[ 62700-61-2 ]

References: [1]Journal of the Chemical Society,1958,p. 804,806.
[2]Journal of Medicinal Chemistry,1996,vol. 39,p. 2 - 9.

26
[ 6972-82-3 ]
[ 10184-42-6 ]

References: [1]Justus Liebigs Annalen der Chemie,1923,vol. 432,p. 287.

27
[ 6972-78-7 ]
[ 6972-82-3 ]

Yield	Reaction Conditions	Operation in experiment
92.3%	With hydrogen; In isopropyl alcohol; at 55℃; under 2250.23 Torr; for 2h;	To further increase the conversion rate of the reaction, Catalytic reduction of 6-amino-5-nitroso-1-methyluracil The reaction system of 5,6-diamino-1-methyluracil was optimized, and in order to obtain a high separation yield, the post-reaction treatment was also optimized. The optimized steps were: 1) 0.4 g of ammonium metatungstate modified palladium metal catalyst (prepared in Example 1), Substrate 6-amino-5-nitroso-1-methyl uracil 10.0g was added to 80ml of isopropanol and stirred in the hydrogenation reactor; 2) Nitrogen replaces the air in the hydrogenation reactor three times, and then adjusts the temperature of the hydrogenation reactor to 55°C. (Hydrogen pressure is 0.3 MPa), the reaction was taken 2h after the reaction solution was subjected to HPLC (HPLC assay result was 99.6percent conversion, selectivity 98.3percent), stirring was stopped, hydrogen pressure was removed, and the temperature was lowered to room temperature; 3) Filtrate, remove the catalyst by filtration, collect the filtrate and heat up to 50-60 °C (after treatment; 4) Add purified water to the post-treatment solution, stop the dripping when turbidity has appeared, and incubate for 2h, then continue dropping. When water is no longer crystallized (a total of 45 ml of water is dropped, 10 ml is added when turbid, and 35 ml is added dropwise), the temperature is lowered to 10° C., filtered and dried to give pale yellow 5,6-diamino-1 -methyl uracil ( The weight yield was 92.3percent, and the volume purity was 99.4percent).
87.9%	With ammonium hydroxide; sodium dithionite; at 25 - 60℃; for 7h;	6-Amino-5-nitroso-1-methyluracil 2a (11.50 g, 67.6 mmol) was dissolved in 200 mL of aqueous ammonia (25percent)in,Sodium dithionite (41.20 g, 236.6 mmol) was added at room temperature 25 ° C and stirred. The temperature in the reaction flask was gradually increased to 35 °C. When the temperature inside the bottle no longer rises, it is heated to 60 ° C and stirred for 1 h.The reaction was then moved to room temperature and stirred for 6 h. After the reaction was completed, the stirring was stopped, filtered, and the cake was washed with ice water and dried in vacuo. Intermediate 3a was obtained as a white solid 9.28 g, yield 87.9percent.
	With ammonium hydroxide; sodium dithionite; In water; at 30 - 50℃;	Na2S204 (13.0 g, 74.1 mmol) was added in several portions to a suspension of 6-amino- l-methyl-5-nitrosopyrimidine-2,4(lH,3H)-dione (4.20 g, 24.7 mmol) in saturated ammonium hydroxide solution (42 mL) at 30 °C. After the addition was complete, the reaction was warmed to 50 °C and stirred for 2 hours. The reaction was then cooled to room temperature. The solidwas collected by filtration, washed with water, and dried in vacuo to afford 5,6-diamino-l- methylpyrimidine-2,4(lH,3H)-dione. MS (APCI) = 157 (M+l)+

	With diammonium sulfide; at 70 - 80℃; for 0.25h;	General procedure: Compounds 3a?e were prepared by the same reported method.33,34 Thenitroso analogues 2a?e of compounds 1a?e [obtained by the additionof a mixture of acetic acid (3 mL) and sodium nitrite (4.60 mmol) inwater (2.0 mL) to compound 1a?e suspended in water (20 mL) withstirring at room temperature. The formed coloured nitroso analogue2a?e was filtered, washed with water and dried in a desiccator](8.12 mmol) was added over 15 min to (NH4)2S solution (40.0 mL)at 70?80 °C with stirring. The resulting precipitate was collected byfiltration, washed with ether and dried in a vacuum desiccator to affordthe diaminouracil analogues 3a?e.
	With sodium dithionite; In methanol; water;Reflux;	Compound 1a (2 g, 12 mmol) was dissolved in a mixed solvent of methanol (40 mL) and water (40 mL), and sodium dithionite (6 g, 36 mmol) was added.The reaction was refluxed overnight until the color of Compound 2a disappeared. After the reaction is complete,The solvent was evaporated under reduced pressure. Due to the instability of the diamino group,Compound 1b is used directly for the synthesis of compound 1c after removal of the solvent.

References: [1]Russian Journal of Applied Chemistry,1994,vol. 67,p. 1223 - 1224.
Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation),1994,vol. 67,p. 1389 - 1391.
[2]Chemical and Pharmaceutical Bulletin,2013,vol. 61,p. 477 - 482.
[3]Patent: CN107987028,2018,A .Location in patent: Paragraph 0022.
[4]Patent: CN104211702,2018,B .Location in patent: Paragraph 0173; 0178; 0179.
[5]Journal of Medicinal Chemistry,2009,vol. 52,p. 6433 - 6446.
[6]Bulletin de la Societe Chimique de France,1946,p. 80,82,85.
[7]Journal of the Chemical Society,1958,p. 804,806.
[8]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1954,vol. 74,p. 674,676,678,681.
Chem.Abstr.,1954,p. 10743.
[9]European Journal of Medicinal Chemistry,1990,vol. 25,p. 653 - 658.
[10]Journal of Medicinal Chemistry,1996,vol. 39,p. 2 - 9.
[11]Journal of Molecular Structure,1997,vol. 435,p. 133 - 141.
[12]Tetrahedron Letters,2006,vol. 47,p. 775 - 778.
[13]Journal of labelled compounds and radiopharmaceuticals,2007,vol. 50,p. 33 - 41.
[14]Journal of Medicinal Chemistry,2002,vol. 45,p. 3440 - 3450.
[15]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1397 - 1401.
[16]Patent: EP1193257,2002,A2 .Location in patent: Page 21.
[17]Patent: WO2014/123882,2014,A1 .Location in patent: Page/Page column 98-99.
[18]Journal of Chemical Research,2016,vol. 40,p. 771 - 777.
[19]Patent: CN108358925,2018,A .Location in patent: Paragraph 0040; 0041; 0044; 0045.

28
[ 54058-36-5 ]
[ 6972-82-3 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1956,vol. 76,p. 1107.
Chem.Abstr.,1957,p. 3614.
[2]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1956,vol. 76,p. 1107.
Chem.Abstr.,1957,p. 3614.

29
[ 6972-82-3 ]
[ 2648-71-7 ]
[ 25716-22-7 ]

References: [1]Journal of the Chemical Society C: Organic,1970,p. 437 - 444.

30
[ 6972-82-3 ]
[ 447-31-4 ]
[ 25716-27-2 ]

References: [1]Journal of the Chemical Society C: Organic,1970,p. 437 - 444.

31
[ 6972-82-3 ]
[ 814-75-5 ]
[ 25716-26-1 ]

References: [1]Journal of the Chemical Society C: Organic,1970,p. 437 - 444.

32
[ 6972-82-3 ]
[ 90993-91-2 ]

References: [1]Journal of general chemistry of the USSR,1961,vol. 31,p. 2798 - 2800.
Zhurnal Obshchei Khimii,1961,vol. 31,p. 3000 - 3003.

33
[ 64-18-6 ]
[ 6972-82-3 ]
[ 1076-22-8 ]

Yield	Reaction Conditions	Operation in experiment
94.1%		5,6-Diamino-1-methyluracil 3a (10.00 g, 64.0 mmol) was dissolved in formic acid (3.305 mL) and water(74.74 mL) in a mixed solvent,After heating at 105 C for 3 h, the temperature was lowered to 20 C.Add sodium hydroxide (5.12g,A solution of 128.1 mmol of water (6.40 mL) was heated at 105 C for 1 h and then the reaction was completed. Cool to 0 C, adjust the pH to 4 with glacial acetic acid, precipitate a yellow-white solid, filter, wash the filter cake with ice water,Drying in vacuo gave Intermediate 4a as a white solid (10.01 g).
80%		Add intermediate IV (4g, 25.6mmol) and distilled water (160ml) to a 500ml reaction flask, add formic acid (2.88ml, 76.8mmol), protect with nitrogen, heat reflux for 3h, cool to room temperature, add sodium hydroxide (5.12g) , 128 mmol) aqueous solution, continued reflux for 1 h, the reaction solution was cooled to room temperature, adjusted to pH 7 with 2 mol / L hydrochloric acid, stirred for 1 h in an ice bath, filtered, and the filter cake was washed with ice water (10 ml) and ice ethanol (20 ml), Dry to give a pale yellow solid (3.4 g, 80%).

References: [1]Patent: CN104211702,2018,B .Location in patent: Paragraph 0173; 0174; 0181; 0182.
[2]Patent: CN108299436,2018,A .Location in patent: Paragraph 0142; 0149; 0150.
[3]Journal of Medicinal Chemistry,2009,vol. 52,p. 6433 - 6446.
[4]European Journal of Medicinal Chemistry,1990,vol. 25,p. 653 - 658.

34
[ 6972-78-7 ]
[ 6972-82-3 ]
5,6-Diimino-1-methyl-dihydro-pyrimidine-2,4-dione [ No CAS ]
6-Amino-5-hydroxyamino-1-methyl-1H-pyrimidine-2,4-dione [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1982,vol. 47,p. 196 - 202.

35
[ 617-35-6 ]
[ 6972-82-3 ]
[ 2625-22-1 ]

References: [1]Tetrahedron,1994,vol. 50,p. 13511 - 13522.

36
[ 6972-82-3 ]
[ 4437-51-8 ]
[ 172751-05-2 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2 - 9.
[2]Patent: EP1193257,2002,A2 .Location in patent: Page 22.

37
[ 6972-82-3 ]
[ 131543-46-9 ]
[ 50256-18-3 ]

Yield	Reaction Conditions	Operation in experiment
79%	In water; at 25 - 60℃; for 16h;	5,6-Diamino-1-methylpyrimidine-2,4-dione (4.00 g, 25.6 mmol) was dissolved in water (150 mL). Glyoxal (5.58 g, 38.4 mmol, 40percent aqueous solution) was added in one portion at 25°C. The reaction solution was heated to 60°C for 16 hours. The resulting solid was washed with water (50 mL) to give the product 1-methylpteridine-2,4-dione (3.60 g, as a yellow solid) with a yield of 79percent.
79%	In water; at 25 - 60℃; for 16h;	5,6-Diamino-1-methylpyrimidin-2,4-dione (4.00 g, 25.6 mmol) was dissolved in water (150 mL), and then glyoxal (5.58 g, 38.4 mmol, 40percent aqueous solution) was added at one time at 25° C. The reaction solution was heated to 60° C. and stirred for 16 hours, and then filtered. The solid obtained was washed with water (50 mL) to give a product 1-methylpteridin-2,4-dione (3.60 g, yellow solid) with a yield of 79percent.

References: [1]Patent: EP3299371,2018,A1 .Location in patent: Paragraph 0587; 0590.
[2]Patent: US2018/148451,2018,A1 .Location in patent: Paragraph 0331; 0334.
[3]Journal of Medicinal Chemistry,1996,vol. 39,p. 2 - 9.

38
[ 6972-82-3 ]
[ 762-42-5 ]
6-amino-5-(1,2-(E)-dicarbomethoxyvinyl)amino-1-methylpyrimidine-2,4(1H,3H)-dione [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1999,vol. 36,p. 435 - 440.

41
1-methyl-2.4-dioxo-6-imino-5-hydroxyimino-hexahydropyrimidine [ No CAS ]
[ 6972-82-3 ]

References: [1]Chemische Berichte,1900,vol. 33,p. 3047.
    Chemisches Zentralblatt,1901,vol. 72,p. 548.
[2]Patent: DE166267, .
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 8,p. 1139.
[3]Patent: DE161493, .
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 8,p. 1137.

42
[ 14371-10-9 ]
[ 6972-82-3 ]
[ 343362-39-0 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3440 - 3450.

43
[ 6972-82-3 ]
[ 194602-23-8 ]
8-[2-ethoxy-5-(4-methyl-piperazine-1-sulfonyl)-phenyl]-3-methyl-3,7-dihydro-purine-2,6-dione [ No CAS ]