87486-33-7|3,5-Dichloro-1-methylpyrazin-2(1H)-one| Ambeed

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Quality Control of [ 87486-33-7 ] Purity: 98% SDS Specification

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Product Details of [ 87486-33-7 ]

CAS No. :	87486-33-7
Formula :	C₅H₄Cl₂N₂O
M.W :	179.00
SMILES Code :	O=C1C(Cl)=NC(Cl)=CN1C
MDL No. :	MFCD12022618
InChI Key :	QHMYGZJTKUTEAB-UHFFFAOYSA-N
Pubchem ID :	13062968

Safety of [ 87486-33-7 ]

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

Application In Synthesis of [ 87486-33-7 ]

* 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 [ 87486-33-7 ]

[ 87486-33-7 ] Synthesis Path-Downstream 1~37

1
[ 67-56-1 ]
[ 87486-33-7 ]
[ 87486-40-6 ]

References: [1]Tetrahedron,1990,vol. 46,p. 5715 - 5732.

2
[ 79-37-8 ]
[ 25808-30-4 ]
[ 87486-33-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	In chlorobenzene; at 90.0℃;	bl . l) Compound (2) To a solution of cyano-N-methylmethanaminium chloride (6.4 g, 39.9 mmol) in chlorobenzene (50 ml) was added dropwise oxalyl chloride (12 ml, 137 mmol) at r. t., then the resulting solution was heated slowly to 90 C and stirred overnight. The solvent was removed, the residue was purified by column chromatography on silica gel (PE:EA=10: 1) to give the title compound as yellow oil (5 g, 70% yield). LC-MS (ESI+): m/e 178 (M+H)+, Rt: 1.54 min.
60%	In 1,2-dichloro-benzene; at 80.0℃; for 8.0h;	d) 3,5-Dichloro-1-methyl-1H-pyrazin-2-one (4c)[0245][0246]3.29 g (30.8 mmoles) of methylamino-acetonitrile hydrochloride is placed in the presence of 19.6 g (154 mmoles) of oxalyl chloride in 30 ml of 1,2-dichlorobenzene. The mixture is heated for 8 hours at 80 C. After concentrating the reaction medium to dryness, the residue obtained is purified by flash chromatography (Petroleum ether-CH2Cl2 gradient 100-0 to 0-100). 3.35 g of intermediate 4c is obtained in beige powder form (yield: 60%).[0247]TLC silica gel 60 F 254 Merck, CH2Cl2-MeOH: 90-10, Rf=0.79.
	In chloroform;Reflux;	Step 1. 3,5-dichloro-1-methylpyrazin-2(1H)-one(Methylamino)acetonitrile hydrochloride (2.55 g, 23.9 mmol) was dissolved in chloroform in a 1-neck round-bottom flask (38.93 mL, 486.5 mmol) and oxalyl chloride (6.07 mL, 71.8 mmol) was added. The reaction was heated to reflux overnight and was transferred into a different flask, and the solvent removed by rotary evaporation. The reaction was chromatographed on silica gel using 1:1 EtOAc/hexanes to give the product. Mass spec: [M+1]: 179. 1H NMR (CDCl3): 7.25 (s, 1H), 3.60 (s, 3H).

References: [1]Patent: WO2014/140184,2014,A1 .Location in patent: Page/Page column 75.
[2]Patent: US2013/40928,2013,A1 .Location in patent: Paragraph 0245; 0246; 0247.
[3]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 919 - 923.
[4]Patent: US2010/298334,2010,A1 .Location in patent: Page/Page column 56.

3
[ 917-58-8 ]
[ 87486-33-7 ]
[ 87486-46-2 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 919 - 923.

4
[ 87486-33-7 ]
[ 106718-85-8 ]

References: [1]Tetrahedron,1990,vol. 46,p. 5715 - 5732.

5
[ 87486-33-7 ]
[ 87486-43-9 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In 1,4-dioxane;	EXAMPLE 2 3-Amino-5-chloro-1-methyl-2(1H)-pyrazinone A solution of <strong>[87486-33-7]3,5-dichloro-1-methyl-2(1H)-pyrazinone</strong> (7.16 g, 0.040 mol) in dioxane (120 mL) was treated with a concentrated aqueous solution of ammonia (28%, 16 mL, 0.24 mol). After stirring at room temperature for three days a suspension of solid had formed. The solid was collected, rinsed with a little water, ether, and hexanes and air dried. The product, 3-amino-5-chloro-1-methyl-2(1H)-pyrazinone, was obtained as a white crystalline powder (4.81 g) melting above 250 C. PMR (DMSO-d6, 200 MHz): delta 7.16 (broad s, 2H, NH2); 6.99 (s, 1H, Het-H); 3.34 (s, 3H, N--CH3). IR (Nujol mull): 3310 (w, NH); 3170 (w, NH); 1660 (s, C=O) cm-1.

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 919 - 923.
[2]Patent: US4802908,1989,A .

6
[ 87486-33-7 ]
[ 87486-41-7 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 919 - 923.

7
[ 87486-33-7 ]
[ 98078-35-4 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 229 - 234.

8
[ 87486-33-7 ]
[ 109-89-7 ]
[ 139706-33-5 ]

References: [1]Journal of Organic Chemistry,1992,vol. 57,p. 2935 - 2937.

9
[ 87486-33-7 ]
[ 17356-08-0 ]
[ 107363-42-8 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 113 - 118.

10
[ 87486-33-7 ]
[ 536-74-3 ]
[ 130879-50-4 ]
[ 130879-49-1 ]

References: [1]Tetrahedron,1990,vol. 46,p. 5715 - 5732.
[2]Tetrahedron,1990,vol. 46,p. 5715 - 5732.

11
[ 87486-33-7 ]
[ 762-42-5 ]
[ 106718-99-4 ]
[ 130879-33-3 ]

References: [1]Tetrahedron,1990,vol. 46,p. 5715 - 5732.
[2]Tetrahedron,1990,vol. 46,p. 5715 - 5732.
[3]Tetrahedron Letters,1986,vol. 27,p. 2509 - 2512.

12
[ 87486-33-7 ]
[ 762-42-5 ]
[ 106719-09-9 ]

References: [1]Tetrahedron,1990,vol. 46,p. 5715 - 5732.

13
[ 87486-33-7 ]
[ 762-42-5 ]
[ 106719-09-9 ]

References: [1]Tetrahedron Letters,1986,vol. 27,p. 2509 - 2512.

14
[ 87486-33-7 ]
[ 623-47-2 ]
[ 130879-39-9 ]
[ 130879-40-2 ]

References: [1]Tetrahedron,1990,vol. 46,p. 5715 - 5732.
[2]Tetrahedron,1990,vol. 46,p. 5715 - 5732.

15
[ 557-66-4 ]
[ 87486-33-7 ]
5-chloro-3-(ethylamino)-1-methyl-2(1H)-pyrazinone [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 304 - 308.

16
[ 87486-33-7 ]
[ 139706-36-8 ]

References: [1]Journal of Organic Chemistry,1992,vol. 57,p. 2935 - 2937.

17
[ 87486-33-7 ]
[ 87486-40-6 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 919 - 923.

18
[ 87486-33-7 ]
[ 87486-42-8 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 919 - 923.

19
[ 87486-33-7 ]
[ 107363-44-0 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 113 - 118.

20
[ 87486-33-7 ]
[ 107363-46-2 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 113 - 118.

21
[ 87486-33-7 ]
[ 107363-48-4 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 113 - 118.

22
[ 87486-33-7 ]
[ 98078-19-4 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 229 - 234.

23
[ 87486-33-7 ]
[ 98078-20-7 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 229 - 234.

24
[ 87486-33-7 ]
[ 98078-21-8 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 229 - 234.

25
[ 87486-33-7 ]
[ 98078-22-9 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 229 - 234.

26
[ 87486-33-7 ]
[ 107363-51-9 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 113 - 118.

27
[ 87486-33-7 ]
[ 107363-54-2 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 113 - 118.

28
[ 87486-33-7 ]
[ 107363-53-1 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 113 - 118.

29
[ 87486-33-7 ]
[ 107363-56-4 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 113 - 118.

30
[ 87486-33-7 ]
[ 130879-56-0 ]

References: [1]Tetrahedron,1990,vol. 46,p. 5715 - 5732.

31
[ 87486-33-7 ]
[ 130879-60-6 ]

References: [1]Tetrahedron,1990,vol. 46,p. 5715 - 5732.

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 1 3,5-Dichloro-1-methyl-2(1H)-pyrazinone Methylaminoacetonitrile hydrochloride (159.78 g, 1.50 mol) was added in one portion to a solution of oxalyl chloride (654.3 mL, 7.50 mol) in anhydrous chlorobenzene (2000 mL). The mixture was heated at 80 C. for 8 hours. The solvent was then rotary evaporated, and the residue was taken up in CH2 Cl2 and preabsorbed onto silica gel. Flash chromatography using 6:3:1 dichloromethane-hexanes-ether solvent mixture as eluant gave a partially purified product that was further purified by chromatography on silica gel using a 8:1:1 dichloromethane-hexane-ether solvent mixture as eluant. Finally, crystallization from a mixture of ether, 1-chlorobutane; and hexanes furnished the product as a pale yellow, dense crystalline powder melting at 65-67. The yield of 3,5-dichloro-1-methyl-2(1H)-pyrazinone was 101.60 g. PMR (CDCl3, 200 MHz); delta 7.26 (s, 1H, Het-H); 3.60 (s, 3H, N--CH3). IR (Nujol mull): 1660 (s, C=O) cm-1.

33
[ 941687-74-7 ]
[ 87486-33-7 ]
[ 1257069-94-5 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; at 100.0℃; for 2.0h;	Step 2. +/-3-[1-(6-chloro-4-methyl-3-oxo-3,4-dihydropyrazin-2-yl)pyrrolidin-3-yl]-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile3-Pyrrolidin-3-yl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (50.00 mg, 0.1142 mmol, prepared as in Example 15, Steps 1-3, omitting the chiral separation performed in Step 2) was mixed with <strong>[87486-33-7]3,5-dichloro-1-methylpyrazin-2(1H)-one</strong> (32.00 mg, 0.1788 mmol) and was dissolved in 1,4-dioxane (0.5 mL). The reaction was heated at 100 C. for 2 h at which time LCMS analysis showed mainly product. The residues were chromatographed on silica gel using EtOAc and 5% MeOH/EtOAc to give the product. Mass spec: [M+1]: 580.

References: [1]Patent: US2010/298334,2010,A1 .Location in patent: Page/Page column 56.

34
[ 941687-74-7 ]
[ 87486-33-7 ]
[ 1257073-31-6 ]

References: [1]Patent: US2010/298334,2010,A1 .

35
(2-trifluoromethyl-phenyl)-piperazin-1-yl-methanone hydrochloride [ No CAS ]
[ 87486-33-7 ]
[ 1343889-30-4 ]

Yield	Reaction Conditions	Operation in experiment
36%	With triethylamine; In butan-1-ol; at 120.0℃; for 24.0h;	General procedure: 6?-Chloro-4?-methyl-4-(2-trifluoromethyl-benzoyl)-3,4,5,6-tetrahydro-2H,4?H-[1,2?]bipyrazinyl-3?-one (1)[0262][0263]Compound 1 is prepared according to synthesis method 1: 1.76 g (5.97 mmoles) of derivative 1 h and 1.13 g (6.31 mmoles) of pyrazinone 4c are placed in 3 ml of butanol-1 in the presence of 4 ml (27.9 mmoles) of NEt3. This mixture is stirred at 120 C. for 24 hours. After concentrating the reaction medium to dryness, the residue obtained is taken up with AcOEt and washed with water and with a saturated NaCl solution. After drying on MgSO4, the organic phase is concentrated to dryness. The residue obtained is purified by silica flash chromatography (CH2Cl2-AcOEt gradient: 100-0 to 90-10). 0.86 g of beige solid is isolated (yield: 36%).[0264]TLC silica gel 60 F 254 Merck, CH2Cl2-MeOH: 95-5, Rf=0.71.[0265]F=162 C.[0266]1H NMR (CDCl3) ppm: 3.28 (t, 2H, J=5.18 Hz), 3.44 (s, 3H), 3.67-3.88 (m, 3H), 3.93-4.09 (m, 3H), 6.73 (s, 1H), 7.35 (d, 1H, J=7.6 Hz), 7.54 (t, 1H, J=7.6 Hz), 7.62 (t, 1H, J=7.6 Hz), 7.73 (d, 1H J=8 Hz).[0267]MS (+ESI) m/z 401 (MH+)

References: [1]Patent: US2013/40928,2013,A1 .Location in patent: Paragraph 0262; 0263; 0264; 0265; 0266; 0267.

36
[ 87486-33-7 ]
[ 762-42-5 ]
[ 130879-33-3 ]

Yield	Reaction Conditions	Operation in experiment
50.8%	In 5,5-dimethyl-1,3-cyclohexadiene; at 145.0℃;	bl .2) Compound (3) A solution of compound (2) (40 g, 223 mmol) and 2-butynedioic acid dimethyl ester (950 g, 670 mmol) in xylene (400 ml) was heated at 145C overnight. The mixture was allowed to cool to r.t.. The reaction mixture was filtered to afford compound (3) (29.5 g, 50.8% yield). LC-MS (ESI+): m/e 260 (M+H)+, Rt: 1.50 min; 1H- NMR(DMSO-

References: [1]Patent: WO2014/140184,2014,A1 .Location in patent: Page/Page column 75-76.

37
[ 594-27-4 ]
[ 87486-33-7 ]
5-chloro-1,3-dimethylpyrazin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 150.0℃; for 0.333333h;Sealed tube; Microwave irradiation;	A solution containing 3,5-dichloro-l-methylpyrazin-2(lH)-one (300 mg, 1.676 mmol) (CAS 87486-33-7), tetramethyltin (0.256 mL, 1.844 mmol) and tetrakis(triphenylphosphine)palladium(0) (48.4 mg, 0.042 mmol) in DMF (2 mL) in a Biotage microwave vial was sealed with a Teflon-lined septa cap. The vial was evacuated under vacuum and backfilled with nitrogen gas, using a needle from a vacuum manifold. The procedure repeated and the nitrogen line removed. The vial was heated in a Biotage microwave at 150 C for 20 min. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (50 mL) and washed with aqueous 10% NaF solution (2x10 mL) and saturated aqueous NaCl solution (1x10 mL), dried (Na2S04), filtered and concentrated. The crude product was dissolved in a small amount of DCM and charged to a 10 g ISCO silica gel column, placed on a Teledyne ISCO system and eluted over a 20 min gradient using 0%-100% hexanes/ethyl acetate eluent to afford 5- chloro-l,3-dimethylpyrazin-2(lH)-one (170 mg, 1.072 mmol, 64.0 % yield). LCMS MH+: 159.0. HPLC Ret. Time 0.52 min. Method Bl. NMR (400 MHz, CHLOROFORM-d) delta 7.13 (bm, 1H), 3.52 (s, 3H), 2.48 (d, J=0.6 Hz, 3H). Fragment 21 : 6-Chloro-2,4,5-trimethylpyridazin-3(2H)-one

References: [1]Patent: WO2019/28302,2019,A1 .Location in patent: Page/Page column 63.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
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

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CAS No.: 87486-33-7

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CAS No.: 87486-33-7

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[ 87486-33-7 ] Synthesis Path-Downstream 1~37

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