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Quality Control of [ 131052-40-9 ] Purity: 98% SDS Specification

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Product Details of [ 131052-40-9 ]

CAS No. :	131052-40-9
Formula :	C₁₂H₁₆N₂O₄
M.W :	252.27
SMILES Code :	O=C(C1=NC=C(NC(OC(C)(C)C)=O)C=C1)OC
MDL No. :	MFCD16036517
InChI Key :	GPVMPPDFEOSPND-UHFFFAOYSA-N
Pubchem ID :	14842342

Safety of [ 131052-40-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 131052-40-9 ]

* 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.

Upstream synthesis route of [ 131052-40-9 ]
Downstream synthetic route of [ 131052-40-9 ]

[ 131052-40-9 ] Synthesis Path-Upstream 1~1

1
[ 131052-40-9 ]
[ 323578-38-7 ]

Yield	Reaction Conditions	Operation in experiment
67%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 12 h; Inert atmosphere	Step 3. tert-Butyl (6-(hydroxymethyl)pyridin-3-yl)carbamate. LAH powder (36 g, 0.96 mol) was suspended in dry THF (1000 ml) under N₂atmosphere and cooled to 0° C. To the mixture was added compound 3 (150 g, 0.60 mol) in dry THF (1000 ml) slowly at 0° C. The reaction mixture was gradually warmed to room temperature and stirred for 12 h. TLC (PE/EA, 1:1) showed that the reaction was complete, and the reaction was quenched with dropwise addition of THF-Water (9:1, 400 mL) followed by 90 ml 15percent NaOH aqueous and 50 ml of water at 0° C., stirred for 0.5 h at room temperature, and filtered through a pad of Celite®, and then washed with THF (4×1000 ml). The filtrate was concentrated under reduced pressure to give the crude which was purified by column chromatography over silica gel eluting with PE/EA (2:1-1:2). The desired fraction was concentrated to afford tert-butyl (6-(hydroxymethyl)pyridin-3-yl)carbamate (450 g, 67percent) as a white solid. ¹H NMR (400 MHz, DMSO-d₆) δ 9.58-9.40 (m, 1H), 8.59-8.45 (m, 1H), 7.95-7.78 (m, 1H), 7.42-7.22 (m, 1H), 5.42-5.21 (m, 1H), 4.58-4.40 (m, 2H), 1.48 (s, 9H).
60%	With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 12 h; Inert atmosphere	To a stirred solution of methyl 5-[(tert-butoxy)carbonyl]amino}pyridine-2- carboxylate (EV-AX4571-001, 2.73 g, 10.82 mmol) in THF (60 ml) at 0 °C under an atmosphere of nitrogen was added 4M lithium tetrahydridoaluminate(l-) in diethyl ether (4.1 ml) drop-wise, the reaction was allowed to warm to room temperature and stirred for a further 12h. The reaction was quenched by addition of THF:water (9: 1, 15 ml), followed by 10percent sodium hydroxide (10 ml) and then water (10 ml). The reaction mixture was then filtered through a pad of Kieselguhr, rinsing with THF (3 x 50 ml). The filtrate was concentrated in vacuo and the crude was purified by flash column chromatography (50-100percent) EtOAc/heptane then 0-10percent Methanol/EtOAc) to obtain 1.50 g (60percent) of tert-butyl N-[6- (hydroxymethyl)pyridin-3-yl]carbamate EV-AX4573-001 as an off-white solid. LCMS (method D): retention time 0.70min, M/z = 224 (M + 1).

References: [1] European Journal of Inorganic Chemistry, 2010, # 13, p. 1913 - 1928.
[2] Patent: US2015/158864, 2015, A1, . Location in patent: Paragraph 0295.
[3] Patent: WO2017/100594, 2017, A1, . Location in patent: Paragraph 00304.
[4] Patent: WO2006/51270, 2006, A1, . Location in patent: Page/Page column 146.

[ 131052-40-9 ] Synthesis Path-Downstream 1~2

1
[ 131052-40-9 ]
[ 323578-38-7 ]

Yield	Reaction Conditions	Operation in experiment
67%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 12h;Inert atmosphere;	Step 3. tert-Butyl (6-(hydroxymethyl)pyridin-3-yl)carbamate. LAH powder (36 g, 0.96 mol) was suspended in dry THF (1000 ml) under N2 atmosphere and cooled to 0 C. To the mixture was added compound 3 (150 g, 0.60 mol) in dry THF (1000 ml) slowly at 0 C. The reaction mixture was gradually warmed to room temperature and stirred for 12 h. TLC (PE/EA, 1:1) showed that the reaction was complete, and the reaction was quenched with dropwise addition of THF-Water (9:1, 400 mL) followed by 90 ml 15% NaOH aqueous and 50 ml of water at 0 C., stirred for 0.5 h at room temperature, and filtered through a pad of Celite, and then washed with THF (4×1000 ml). The filtrate was concentrated under reduced pressure to give the crude which was purified by column chromatography over silica gel eluting with PE/EA (2:1-1:2). The desired fraction was concentrated to afford tert-butyl (6-(hydroxymethyl)pyridin-3-yl)carbamate (450 g, 67%) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 9.58-9.40 (m, 1H), 8.59-8.45 (m, 1H), 7.95-7.78 (m, 1H), 7.42-7.22 (m, 1H), 5.42-5.21 (m, 1H), 4.58-4.40 (m, 2H), 1.48 (s, 9H).
60%	With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at 0 - 20℃; for 12h;Inert atmosphere;	To a stirred solution of methyl 5-[(tert-butoxy)carbonyl]amino}pyridine-2- carboxylate (EV-AX4571-001, 2.73 g, 10.82 mmol) in THF (60 ml) at 0 C under an atmosphere of nitrogen was added 4M lithium tetrahydridoaluminate(l-) in diethyl ether (4.1 ml) drop-wise, the reaction was allowed to warm to room temperature and stirred for a further 12h. The reaction was quenched by addition of THF:water (9: 1, 15 ml), followed by 10% sodium hydroxide (10 ml) and then water (10 ml). The reaction mixture was then filtered through a pad of Kieselguhr, rinsing with THF (3 x 50 ml). The filtrate was concentrated in vacuo and the crude was purified by flash column chromatography (50-100%) EtOAc/heptane then 0-10% Methanol/EtOAc) to obtain 1.50 g (60%) of tert-butyl N-[6- (hydroxymethyl)pyridin-3-yl]carbamate EV-AX4573-001 as an off-white solid. LCMS (method D): retention time 0.70min, M/z = 224 (M + 1).
		Methyl 5-tert-butoxycarbonylaminopyridine-2-carboxylate (J. Med. Chem., 1991, 34, 1594; 5 g) was dissolved in THF (75 mL) and the mixture was cooled to 00C. Lithium aluminium hydride (IM in THF, 19.8 mL) was added dropwise and the mixture was stirred at room temperature for 1 hour. The mixture was re-cooled to 0C and water (0.75 mL) was carefully added followed in turn by 2Nu aqueous sodium hydroxide solution (0.75 mL) and water (2.25 mL). The resultant mixture was stirred for 30 minutes and filtered. The filtrate was dried over magnesium sulfate and evaporated. There was thus obtained 5-tert-butoxycarbonylamino-2-hydroxymethylpyridine as a solid (2.8 g); 1H NMR Spectrum: (DMSOd6) 1.47 (s, 9H), 4.46 (d, 2H), 5.24 (t, IH), 7.33 (d, IH), 7.84 (m, IH), 8.49 (d, IH), 9.44 (s, IH); Mass Spectrum: M+H+ 225.

References: [1]European Journal of Inorganic Chemistry,2010,p. 1913 - 1928.
[2]Patent: US2015/158864,2015,A1 .Location in patent: Paragraph 0295.
[3]Patent: WO2017/100594,2017,A1 .Location in patent: Paragraph 00304.
[4]Patent: WO2006/51270,2006,A1 .Location in patent: Page/Page column 146.

2
[ 24242-20-4 ]
[ 131052-40-9 ]

References: [1]Patent: US2015/158864,2015,A1 .
[2]Patent: WO2016/33445,2016,A1 .

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Preparation of Amines • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

Related Functional Groups of
[ 131052-40-9 ]

Esters

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Related Parent Nucleus of
[ 131052-40-9 ]

Pyridines

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5-((tert-Butoxycarbonyl)amino)picolinic acid

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