103976-52-9|2-(Methylamino)nicotinamide| Ambeed

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Quality Control of [ 103976-52-9 ] Purity: 97% SDS Specification

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Product Details of [ 103976-52-9 ]

CAS No. :	103976-52-9
Formula :	C₇H₉N₃O
M.W :	151.17
SMILES Code :	O=C(N)C1=C(NC)N=CC=C1
MDL No. :	MFCD11052030
InChI Key :	DVBVURADALKRQB-UHFFFAOYSA-N
Pubchem ID :	13466149

Safety of [ 103976-52-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 103976-52-9 ]

* 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 [ 103976-52-9 ]

[ 103976-52-9 ] Synthesis Path-Downstream 1~19

1
[ 37960-59-1 ]
[ 103976-52-9 ]
[ 103976-51-8 ]
[ 15936-11-5 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 765 - 769.
[2]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 765 - 769.
[3]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 765 - 769.

2
[ 103976-61-0 ]
[ 103976-52-9 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 765 - 769.

3
[ 2942-59-8 ]
[ 103976-52-9 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 765 - 769.

4
[ 32399-13-6 ]
[ 103976-52-9 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 765 - 769.

5
[ 103976-52-9 ]
[ 103-71-9 ]
[ 142168-85-2 ]

Yield	Reaction Conditions	Operation in experiment
17%	In toluene; at 110.0℃; for 12.0h;	2-(Methylamino)pyridine-3-carboxamide (100 mg, 0.661 mmol) and phenylisocyanate (157 mg, 1.32 mmol) were dissolved in toluene (10 mL) and stirred at 110C for 12 hours. The reaction was quenched by adding water (10 mL) and filtered to give 1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (20.0 mg, as a yellow solid) with a yield of 17%. 1H NMR: (400 MHz, DMSO-d6) δ 11.72(s, 1H), 8.72(d, J = 2.0 Hz, 1H), 8.31(d, J = 7.6 Hz, 1H), 7.29(dd, J = 7.6, 2.0 Hz, 1H), 3.48(s, 3H). MS-ESI calcd. [M + H]+ 178, found 178.
17%	In toluene; at 110.0℃; for 12.0h;	2-(Methylamino)pyridin-3-carboxamide (100 mg, 0.661 mmol) and phenyl isocyanate (157 mg, 1.32 mmol) were dissolved in toluene (10 mL), followed by stirring at 110 C. for 12 hours. The reaction was quenched by adding water (10 mL). The reaction solution was filtered to give 1-methylpyrido[2,3-d]pyrimidin-2,4(1H,3H)-dione (20.0 mg, yellow solid) with a yield of 17%. 1H NMR: (400 MHz, DMSO-d6) δ11.72 (s, 1H), 8.72 (d, J=2.0 Hz, 1H), 8.31 (d, J=7.6 Hz, 1H), 7.29 (dd, J=7.6, 2.0 Hz, 1H), 3.48 (s, 3H). MS-ESI calculated value: [M+H]+ 178; measured value: 178.

References: [1]Patent: EP3299371,2018,A1 .Location in patent: Paragraph 0528; 0531.
[2]Patent: US2018/148451,2018,A1 .Location in patent: Paragraph 0267; 0270.

6
[ 6602-54-6 ]
[ 103976-52-9 ]

References: [1]Patent: US2018/148451,2018,A1 .
[2]Patent: EP3299371,2018,A1 .

7
[ 52583-87-6 ]
[ 103976-52-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	With dihydrogen peroxide; potassium carbonate; In dimethyl sulfoxide; at 20.0℃; for 1.0h;	2-(Methylamino)nicotinonitrile (600 mg, 4.51 mmol), potassium carbonate (1.87 mg, 0.130 mmol) and hydrogen peroxide (0.1 mL) were dissolved in dimethylsulfoxide (10 mL), reacted for 1 hour at room temperature and quenched by the addition of water (10 mL). The reaction solution was extracted with ethyl acetate (10 mL x 3), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure, and purified on a silica gel plate (1: 1 petroleum ether / ethyl acetate, Rf = 0.2) to give 2-(methylamino)pyridine-3-carboxamide (500 mg, white solid) with a yield of 73%. 1H NMR: (400 MHz, DMSO-d6) δ 8.45-8.40(br, 1H), 8.28(d, J = 2.0 Hz, 1H), 7.95-7.93(m, 2H), 7.35-7.30(br, 1H), 6.53(dd, J = 7.6, 2.0 Hz, 1H), 3.03(d, J = 4.8 Hz, 3H). MS-ESI calcd. [M + H]+ 152, found 152.
73%	With dihydrogen peroxide; potassium carbonate; In dimethyl sulfoxide; at 20.0℃; for 1.0h;	2-(Methylamino)nicotinonitrile (600 mg, 4.51 mmol), potassium carbonate (1.87 mg, 0.130 mmol), hydrogen peroxide (0.1 mL) were dissolved in dimethyl sulfoxide (10 mL), followed by reaction at room temperature for 1 hour. The reaction was quenched by adding water (10 mL). The reaction solution was extracted with ethyl acetate (10 mL*3), dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure and then purified by silica gel preparative plate (1:1 petroleum ether/ethyl acetate, Rf-0.2) to give 2-(methylamino)pyridin-3-carboxamide (500 mg, white solid) with a yield of 73%. 1H NMR: (400 MHz, DMSO-d6) δ8.45-8.40 (br, 1H), 8.28 (d, J=2.0 Hz, 1H), 7.95-7.93 (m, 2H), 7.35-7.30 (br, 1H), 6.53 (dd, J=7.6, 2.0 Hz, 1H), 3.03 (d, J=4.8 Hz, 3H). MS-ESI calculated value: [M+H]+ 152; measured value: 152.

References: [1]Patent: EP3299371,2018,A1 .Location in patent: Paragraph 0528; 0530.
[2]Patent: US2018/148451,2018,A1 .Location in patent: Paragraph 0267; 0269.

8
[ 103976-52-9 ]
3-((3-isopropylisoxazol-5-yl)methyl)-1-methylpyrido[2,3-d]pyrimidine-2,4-dione [ No CAS ]

References: [1]Patent: EP3299371,2018,A1 .

9
[ 103976-52-9 ]
3-[3-(1H-indol-3-yl)propyl]-1-methylpyrido[2,3-d]pyrimidine-2,4-dione [ No CAS ]

References: [1]Patent: EP3299371,2018,A1 .

10
[ 103976-52-9 ]
3-(4-(benzofuran-2-yl)butyl)-1-methylpyrido[2,3-d]pyrimidine-2,4-dione [ No CAS ]

References: [1]Patent: EP3299371,2018,A1 .

11
[ 103976-52-9 ]
1-methyl-3-(3-(3-methylisoxazol-5-yl)propyl)pyrido[2,3-d]pyrimidine-2,4-dione [ No CAS ]

References: [1]Patent: EP3299371,2018,A1 .

12
[ 103976-52-9 ]
1-methyl-3-[4-(3-methylisoxazol-5-yl)butyl]pyrido[2,3-d]pyrimidine-2,4-dione [ No CAS ]

References: [1]Patent: EP3299371,2018,A1 .

13
[ 103976-52-9 ]
C₁₅H₁₆N₄O₂S [ No CAS ]

References: [1]Patent: EP3299371,2018,A1 .

14
[ 103976-52-9 ]
1-methyl-3-((3-methyloxetan-3-yl)methyl)pyrido[2,3-d]pyrimidin-2,4-dione [ No CAS ]