[ CAS No. 1791-73-7 ]

Name: 6-Methyl-2,4-pyrimidinediamine
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SKU: A377738
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Quality Control of [ 1791-73-7 ]

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COA GC NMR CNMR HPLC/UPLC LC-MS SDS

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SDS

Product Details of [ 1791-73-7 ]

CAS No. :	1791-73-7	MDL No. :	MFCD00127861
Formula :	C₅H₈N₄	Boiling Point :	389.5°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	HERHQNVDSHUKAK-UHFFFAOYSA-N
M.W :	124.14	Pubchem ID :	229743
Synonyms :

Computed Properties of [ 1791-73-7 ]

TPSA :Topological Polar Surface Area	77.8	H-Bond Acceptor Count :	4
XLogP3 :	-0.1	H-Bond Donor Count :	2
SP3 :	0.20	Rotatable Bond Count :	0

Safety of [ 1791-73-7 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1791-73-7 ]

Upstream synthesis route of [ 1791-73-7 ]
Downstream synthetic route of [ 1791-73-7 ]

[ 1791-73-7 ] Synthesis Path-Upstream 1~8

1
[ 5600-21-5 ]
[ 1791-73-7 ]

Reference： [1] Chemische Berichte, 1901, vol. 34, p. 1242
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 5, p. 940 - 950
[3] Patent: US5521192, 1996, A
[4] Patent: US5622954, 1997, A

2
[ 1118-61-2 ]
[ 50-01-1 ]
[ 1791-73-7 ]

Yield	Reaction Conditions	Operation in experiment
10.5 g	Stage #1: With sodium methylate In methanol at 20℃; for 0.50 h; Stage #2: at 110℃; for 10.00 h; Inert atmosphere	2,4-Diamino-6-methylpyrimidine was synthesized in accordance with the process described in Aust. J. Chem., 1984, vol. 37, pp. 1195-1201. (0362) Guanidine hydrochloride (23.8 g) was added to methanol (50 mL) and a solution of sodium methoxide in 28percent methanol (51 mL), followed by stirring at room temperature for 30 minutes. Subsequently, the precipitated salt was removed by filtration, followed by concentration under reduced pressure to give a guanidine-free product solution. Then, 3-amino crotononitrile (16.4 g) and 1-butanol (60 mL) were added to the solution. The reaction solution was stirred with heating at 110° C. for 10 hours under a nitrogen gas flow. After completion of the reaction, the precipitated salt was removed by hot filtration, and 100 mL of acetone was added to the remaining solution, followed by stirring under ice cooling for 30 minutes to give a crude product. The crude product was recrystallized from acetone to yield 10.5 g of 2,4-diamino-6-methylpyrimidine. (0363) Methyl benzoate (23 g: 169 mmol) and sodium methoxide (22 g: 407 mmol) were added to a solution of 2,4-diamino-6-methylpyrimidine (10 g: 81 mmol) in N-ethylpyrrolidone (100 mL), followed by stirring with heating at 40° C. for 2 hours. The temperature of the reaction system was decreased to room temperature. The reaction solution was poured into a 1N aqueous hydrochloric acid solution, and the solid component was collected by filtration. The crude product was recrystallized from 2-propanol to yield compound (1-2). (0364) The NMR spectrum of produced compound (1-2) is as follows. (0365) ¹H-NMR (solvent: d6-DMSO, standard: tetramethylsilane) δ (ppm) 2.50 (3H, s) 7.45-7.70 (6H, m) 7.90 (1H, s) 7.95-8.05 (4H, m) 10.88 (1H, s) 11.10 (1H, s)

Reference： [1] Australian Journal of Chemistry, 1984, vol. 37, # 6, p. 1195 - 1201
[2] Patent: US2016/159750, 2016, A1. Location in patent: Paragraph 0361-0365

3
[ 5600-21-5 ]
[ 1791-73-7 ]

Reference： [1] Patent: US4083841, 1978, A

4
[ 50-01-1 ]
[ 70807-22-6 ]
[ 1791-73-7 ]

Reference： [1] Organic Process Research and Development, 2013, vol. 17, # 3, p. 427 - 431

5
[ 5424-21-5 ]
[ 1791-73-7 ]

Reference： [1] Chemische Berichte, 1901, vol. 34, p. 1242
[2] Journal of the Chemical Society, 1951, p. 1004,1015[3] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, vol. 24, p. 84

6
[ 3438-46-8 ]
[ 1791-73-7 ]

Reference： [1] Yakugaku Zasshi, 1939, vol. 59, p. 18,26; dtsch. Ref. S. 97, 103, 104[2] Chem.Abstr., 1939, p. 3791

7
[ 5424-21-5 ]
[ 7664-41-7 ]
[ 1791-73-7 ]

Reference： [1] Chemische Berichte, 1899, vol. 32, p. 2934[2] Chemische Berichte, 1902, vol. 35, p. 1570

8
[ 5600-21-5 ]
[ 7664-41-7 ]
[ 1791-73-7 ]

Reference： [1] Chemische Berichte, 1901, vol. 34, p. 1242

[ 1791-73-7 ] Synthesis Path-Downstream 1~10

1
[ 1791-73-7 ]
[ 42399-20-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; ammonium persulfate;	Step B Synthesis of 2,4-diamino-6-methyl-5-pyrimidinyl hydrogen sulfate as an intermediate This compound was prepared in a manner analogous to that of Step C of Example 12, using 30.0 grams (0.242 mole) of 2,4-diamino-6 -methylpyrimidine, 82.8 grams (0.363 mole) of ammonium persulfate and 360 mL of aqueous 5N sodium hydroxide. The product was recrystallized from water, yielding 27.3 grams of 2,4-diamino-6-methyl-5-pyrimidinyl hydrogen sulfate, mp 285 C., dec. The IR spectrum was consistent with the proposed structure.

Reference： [1]Journal of the Chemical Society,1956,p. 2033
[2]Patent: US5521192,1996,A

2
[ 1791-73-7 ]
[ 99419-14-4 ]

Reference： [1]Zhurnal Obshchei Khimii,1954,vol. 24,p. 2212,2214; engl. Ausg. S. 2185, 2186
Zhurnal Obshchei Khimii,1957,vol. 27,p. 2518,2519; engl. Ausg. S. 2576

3
[ 1791-73-7 ]
2,4-diamino-6-methyl-pyrimidine-5-sulfonyl chloride [ No CAS ]

Reference： [1]Zhurnal Obshchei Khimii,1954,vol. 24,p. 2212,2214; engl. Ausg. S. 2185, 2186
Zhurnal Obshchei Khimii,1957,vol. 27,p. 2518,2519; engl. Ausg. S. 2576

4
[ 1791-73-7 ]
[ 2829-59-6 ]

Reference： [1]Chemische Berichte,1901,vol. 34,p. 1242

5
[ 1791-73-7 ]
[ 108-24-7 ]
[ 6344-09-8 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1942,vol. 62,p. 315,333; dtsch. Ref. S. 95, 106
Chem.Abstr.,1951,p. 5150

6
[ 1791-73-7 ]
[ 21416-60-4 ]
6-methyl-<i>N</i>²-picryl-pyrimidine-2,4-diyldiamine [ No CAS ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1940,vol. 60,p. 493,496
S.,vol. 192,p. 195
Chem.Abstr.,1941,p. 743

7
[ 1791-73-7 ]
[ 100-34-5 ]
[ 34289-21-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1959,vol. 7,p. 1,3

8
[ 5600-21-5 ]
[ 1791-73-7 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In methanol;	Step A Synthesis of <strong>[1791-73-7]2,4-diamino-6-methylpyrimidine</strong> as an intermediate A mixture of 50.0 grams (0.348 mole) of 2-amino-4-chloro-6-methylpyrimidine (commercially available) and 100 mL of aqueous 30% ammonia in 400 mL of methanol was placed in a high pressure vessel and heated to 130-165 C. under a pressure of 140-250 psig, where it was stirred for 13 hours. After this time, the reaction mixture was allowed to cool to ambient temperature. The reaction vessel was then opened and the reaction mixture was removed. The reaction vessel was washed with 200 mL of methanol, and the wash was combined with the reaction mixture. The combination was concentrated under reduced pressure to a residual solid. The solid was then stirred for 2 hours at ambient temperature with 100 mL of aqueous 30% ammonia. The mixture was cooled to 0 C., and the solid was collected by filtration. The solid was dried, yielding 40.8 grams of <strong>[1791-73-7]2,4-diamino-6-methylpyrimidine</strong>. The NMR spectrum was consistent with the proposed structure.
	With ammonia; In methanol;	Step A Synthesis of <strong>[1791-73-7]2,4-diamino-6-methylpyrimidine</strong> as an intermediate A mixture of 50.0 grams (0.348 mole) of 2-amino-4-chloro-6-methylpyrimidine (commercially available) and 100 mL of aqueous 30% ammonia in 400 mL of methanol is placed in a high pressure vessel and heated to 130-165 C. under a pressure of 140-250 psig, where it is stirred for 13 hours. After this time, the reaction mixture is allowed to cool to ambient temperature. The reaction vessel is then opened and the reaction mixture is removed. The reaction vessel is washed with 200 mL of methanol, and the wash is combined with the reaction mixture. The combination is concentrated under reduced pressure to a residual solid. The solid is then stirred for 2 hours at ambient temperature with 100 mL of aqueous 30% ammonia. The mixture is cooled to 0 C., and the solid is collected by filtration. The solid is dried, yielding 40.8 grams of <strong>[1791-73-7]2,4-diamino-6-methylpyrimidine</strong>. The NMR spectrum is consistent with the proposed structure.

Reference： [1]Chemische Berichte,1901,vol. 34,p. 1242
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 940 - 950
[3]Patent: US5521192,1996,A
[4]Patent: US5622954,1997,A

9
[ 5424-21-5 ]
[ 1791-73-7 ]

Reference： [1]Chemische Berichte,1901,vol. 34,p. 1242
[2]Journal of the Chemical Society,1951,p. 1004,1015
Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie,vol. 24,p. 84

10
[ 1791-73-7 ]
HNO₃+H₂SO₄ [ No CAS ]
[ 2829-59-6 ]

Reference： [1]Chemische Berichte,1901,vol. 34,p. 1242

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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H401	Toxic to aquatic life
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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1791-73-7 ]

Quality Control of [ 1791-73-7 ]

Related Doc. of [ 1791-73-7 ]

Product Details of [ 1791-73-7 ]

Computed Properties of [ 1791-73-7 ]

Safety of [ 1791-73-7 ]

Application In Synthesis of [ 1791-73-7 ]

[ 1791-73-7 ] Synthesis Path-Upstream 1~8

[ 1791-73-7 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 1791-73-7 ]

Amines

Related Parent Nucleus of [ 1791-73-7 ]

Aromatic Heterocycles

Pyrimidines

Precautionary Statements-General

Prevention

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Physical hazards

Health hazards

Environmental hazards

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[ 1791-73-7 ]