329794-09-4

Basic information

• Product Name: 4-(TERT-BUTYL-DIMETHYL-SILANYLOXYMETHYL)-PYRIDIN-2-YLAMINE
• Synonyms: 4-(TERT-BUTYL-DIMETHYL-SILANYLOXYMETHYL)-PYRIDIN-2-YLAMINE;4-((tert-butyldimethylsilyloxy)methyl)pyridin-2-amine
• CAS NO: 329794-09-4
• Molecular Formula: C₁₂H₂₂N₂OSi
• Molecular Weight: 238.4
• Mol File: 329794-09-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 109.2-109.3°C
• Boiling Point: 320.6 ºC at 760 mmHg
• Flash Point: 147.7 ºC
• Appearance: /
• Density: 0.983 g/cm³
• Vapor Pressure: 0.000315mmHg at 25°C
• Refractive Index: 1.503
• CAS DataBase Reference: 4-(TERT-BUTYL-DIMETHYL-SILANYLOXYMETHYL)-PYRIDIN-2-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(TERT-BUTYL-DIMETHYL-SILANYLOXYMETHYL)-PYRIDIN-2-YLAMINE(329794-09-4)
• EPA Substance Registry System: 4-(TERT-BUTYL-DIMETHYL-SILANYLOXYMETHYL)-PYRIDIN-2-YLAMINE(329794-09-4)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 329794-09-4(Hazardous Substances Data)

Usage

General Description

4-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-ylamine is a chemical compound that contains a pyridine ring with an amine functional group and a silanyloxymethyl substituent. The silanyloxymethyl group consists of a silicon atom bonded to three methyl groups and an oxygen atom. 4-(TERT-BUTYL-DIMETHYL-SILANYLOXYMETHYL)-PYRIDIN-2-YLAMINE is likely to have applications in organic synthesis and chemical processes involving silicon-based reagents. It may also be used in the development of pharmaceuticals and agrochemicals, as well as in the production of advanced materials and specialty chemicals. Its precise properties and potential uses would depend on its specific chemical and structural characteristics, and further research and testing would be needed to determine its full range of potential applications.

InChI:InChI=1/C12H22N2OSi/c1-12(2,3)16(4,5)15-9-10-6-7-14-11(13)8-10/h6-8H,9H2,1-5H3,(H2,13,14)

Synthetic route

tert-butyldimethylsilyl chloride (18162-48-6) + 2-amino-4-hydroxymethylpyridine (105250-17-7) → 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 14h;	86%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 3h;	81%
Stage #1: 2-amino-4-hydroxymethylpyridine With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: tert-butyldimethylsilyl chloride In N,N-dimethyl-formamide at 0℃; for 12h;	62.49%

benzhydrylidene-[4-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-amine → 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4)

Conditions	Yield
With hydroxylamine In methanol at 20℃; for 18h;	17.89 g

(2-chloropyridin-4-yl)methanol (100704-10-7) → 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / imidazole / tetrahydrofuran / 24 h / 20 °C 2: NaOtBu; BINAP racemic; Pd2(dba)3 / toluene / 5 h / 80 °C 3: 17.89 g / aq. hydroxylamine / methanol / 18 h / 20 °C View Scheme

tert-butyldimethylsilyl chloride (18162-48-6) + MeHal → 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / imidazole / tetrahydrofuran / 24 h / 20 °C 2: NaOtBu; BINAP racemic; Pd2(dba)3 / toluene / 5 h / 80 °C 3: 17.89 g / aq. hydroxylamine / methanol / 18 h / 20 °C View Scheme

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloropyridine (787596-40-1) → 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOtBu; BINAP racemic; Pd2(dba)3 / toluene / 5 h / 80 °C 2: 17.89 g / aq. hydroxylamine / methanol / 18 h / 20 °C View Scheme

cyclopropanecarboxylic acid (1759-53-1) + 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → N-(4-(((tert-butyldimethylsilyl)oxy)methyl)pyridin-2-yl)cyclopropanecarboxamide

Conditions	Yield
Stage #1: cyclopropanecarboxylic acid With dmap In dichloromethane for 0.0833333h; Stage #2: 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;	82.1%
Stage #1: cyclopropanecarboxylic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.0833333h; Stage #2: 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine In dichloromethane at 20℃; for 12h;	82%

2-chloro-5-phenyl-thiazole (329794-40-3) + 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → [4-(tert-butyldimethylsilanyloxymethyl)pyridin-2-yl](5-phenylthiazol-2-yl)amine (329794-10-7)

Conditions	Yield
Stage #1: 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 2-chloro-5-phenyl-thiazole In tetrahydrofuran for 2h; Heating;	79%

Benzoyl isothiocyanate (532-55-8) + 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → N-({[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]amino}carbonothioyl)benzamide (872707-10-3)

Conditions	Yield
In toluene at 85℃; for 12h; Heating / reflux;	79%
In toluene at 85℃; for 12h;	79%
In toluene at 85℃; for 12h;	79%

di-tert-butyl dicarbonate (24424-99-5) + 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → tert-butyl (4-(((tert-butyldimethylsilyl)oxy)methyl)pyridin-2-yl)carbamate (864460-81-1)

Conditions	Yield
With pyridine In ethyl acetate; tert-butyl alcohol at 20℃;	62%

6-bromo-2-chloro-benzothiazole (80945-86-4) + 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → 6-bromo-N-(4-(((tert-butyldimethylsilyl)oxy)methyl)pyridin-2-yl)benzo[d]thiazol-2-amine (1377264-31-7)

Conditions	Yield
Stage #1: 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: 6-bromo-2-chloro-benzothiazole In tetrahydrofuran at 65℃; for 2h;	37%

4-cyano-1,2-phenylenediamine (17626-40-3) + 1,1'-Thiocarbonyldiimidazole (6160-65-2) + 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → 2-{[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]amino}-1H-benzimidazole-6-carbonitrile

Conditions	Yield
Stage #1: 1,1'-Thiocarbonyldiimidazole; 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine With 1H-imidazole In dichloromethane at 0 - 20℃; for 72h; Stage #2: 4-cyano-1,2-phenylenediamine In dichloromethane at 20℃; for 2h; Stage #3: With diisopropyl-carbodiimide In dichloromethane at 20℃;	6%

2-chloro-1,3-thiazole-5-carbonitrile (51640-36-9) + 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → [4-(tert-butyldimethylsilanyloxymethyl)pyridin-2-ylamino]thiazole-5-carbonitrile (329794-13-0)

Conditions	Yield
Stage #1: 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine With sodium hydride In tetrahydrofuran for 0.25h; Stage #2: 2-chloro-1,3-thiazole-5-carbonitrile In tetrahydrofuran for 2h; Heating;	23.4 g
With sodium hydride In tetrahydrofuran for 2h; Heating / reflux;
Stage #1: 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine With sodium hydride In tetrahydrofuran for 0.25h; Stage #2: 2-chloro-1,3-thiazole-5-carbonitrile for 2h; Heating / reflux;
With sodium hydride In tetrahydrofuran for 2h; Heating / reflux;

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → 2-(4-chloromethyl-pyridin-2-ylamino)-thiazole-5-carbonitrile (329794-15-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: NaH / tetrahydrofuran / 0.25 h 1.2: 23.4 g / tetrahydrofuran / 2 h / Heating 2.1: hydrogen fluoride-pyridine / tetrahydrofuran / 1 h 3.1: 15.5 g / phosphorus oxychloride; N,N-dimethylformamide / CH2Cl2 / 4 h View Scheme

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → 2-(4-hydroxymethylpyridin-2-ylamino)thiazole-5-carbonitrile (329794-14-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaH / tetrahydrofuran / 0.25 h 1.2: 23.4 g / tetrahydrofuran / 2 h / Heating 2.1: hydrogen fluoride-pyridine / tetrahydrofuran / 1 h View Scheme

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → (4-chloromethylpyridin-2-yl)(5-phenylthiazol-2-yl)amine (329794-12-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: NaH / tetrahydrofuran / 20 °C 1.2: 79 percent / tetrahydrofuran / 2 h / Heating 2.1: 98 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 1 h / 0 °C 3.1: 90 percent / phosphorus oxychloride; N,N-dimethylformamide / CH2Cl2 / 1.5 h View Scheme

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → [2-(5-phenylthiazol-2-ylamino)pyridin-4-yl]methanol (329794-11-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaH / tetrahydrofuran / 20 °C 1.2: 79 percent / tetrahydrofuran / 2 h / Heating 2.1: 98 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 1 h / 0 °C View Scheme

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → 2-(4-morpholin-4-ylmethyl-pyridin-2-ylamino)-thiazole-5-carbonitrile

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaH / tetrahydrofuran / 0.25 h 1.2: 23.4 g / tetrahydrofuran / 2 h / Heating 2.1: hydrogen fluoride-pyridine / tetrahydrofuran / 1 h 3.1: 15.5 g / phosphorus oxychloride; N,N-dimethylformamide / CH2Cl2 / 4 h 4.1: dimethylsulfoxide / 20 °C View Scheme

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → (5-phenyl-thiazol-2-yl)-(4-pyrrolidin-1-ylmethyl-pyridin-2-yl)-amine

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaH / tetrahydrofuran / 20 °C 1.2: 79 percent / tetrahydrofuran / 2 h / Heating 2.1: 98 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 1 h / 0 °C 3.1: 90 percent / phosphorus oxychloride; N,N-dimethylformamide / CH2Cl2 / 1.5 h 4.1: dimethylsulfoxide / 16 h / 20 °C View Scheme

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → 2-(4-piperazin-1-ylmethyl-pyridin-2-ylamino)-thiazole-5-carbonitrile

Conditions	Yield
Multi-step reaction with 5 steps 1.1: NaH / tetrahydrofuran / 0.25 h 1.2: 23.4 g / tetrahydrofuran / 2 h / Heating 2.1: hydrogen fluoride-pyridine / tetrahydrofuran / 1 h 3.1: 15.5 g / phosphorus oxychloride; N,N-dimethylformamide / CH2Cl2 / 4 h 4.1: dimethylsulfoxide / 20 °C 5.1: 0.13 g / HCl (gas) / ethyl acetate / 2.5 h / 0 - 20 °C View Scheme

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → 2-[4-(4-acetyl-piperazin-1-ylmethyl)-pyridin-2-ylamino]-thiazole-5-carbonitrile

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaH / tetrahydrofuran / 0.25 h 1.2: 23.4 g / tetrahydrofuran / 2 h / Heating 2.1: hydrogen fluoride-pyridine / tetrahydrofuran / 1 h 3.1: 15.5 g / phosphorus oxychloride; N,N-dimethylformamide / CH2Cl2 / 4 h 4.1: dimethylsulfoxide / 0.5 h / 20 °C View Scheme

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → 4-({2-[(5-cyano-1,3-thiazol-2-yl)amino]-4-pyridinyl}methyl)-1-piperazinecarboxamide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaH / tetrahydrofuran / 0.25 h 1.2: 23.4 g / tetrahydrofuran / 2 h / Heating 2.1: hydrogen fluoride-pyridine / tetrahydrofuran / 1 h 3.1: 15.5 g / phosphorus oxychloride; N,N-dimethylformamide / CH2Cl2 / 4 h 4.1: dimethylsulfoxide / 20 °C View Scheme

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → 2-[(4-{[4-(methylsulfonyl)piperidin-1-yl]methyl}pyridin-2-yl)amino]-1,3-thiazole-5-carbonitrile

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaH / tetrahydrofuran / 0.25 h 1.2: 23.4 g / tetrahydrofuran / 2 h / Heating 2.1: hydrogen fluoride-pyridine / tetrahydrofuran / 1 h 3.1: 15.5 g / phosphorus oxychloride; N,N-dimethylformamide / CH2Cl2 / 4 h 4.1: 35 percent / diisopropylethylamine / dimethylsulfoxide / 17 h / 20 °C View Scheme

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → 4-({2-[(5-cyano-1,3-thiazol-2-yl)amino]-4-pyridinyl}methyl)-N,N-dimethyl-1-piperazinecarboxamide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaH / tetrahydrofuran / 0.25 h 1.2: 23.4 g / tetrahydrofuran / 2 h / Heating 2.1: hydrogen fluoride-pyridine / tetrahydrofuran / 1 h 3.1: 15.5 g / phosphorus oxychloride; N,N-dimethylformamide / CH2Cl2 / 4 h 4.1: 49 percent / dimethylsulfoxide / 20 °C View Scheme

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → 2-{4-[4-(2-hydroxy-ethanoyl)-piperazin-1-ylmethyl]-pyridin-2-ylamino}-thiazole-5-carbonitrile

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaH / tetrahydrofuran / 0.25 h 1.2: 23.4 g / tetrahydrofuran / 2 h / Heating 2.1: hydrogen fluoride-pyridine / tetrahydrofuran / 1 h 3.1: 15.5 g / phosphorus oxychloride; N,N-dimethylformamide / CH2Cl2 / 4 h 4.1: 33 percent / diisopropylethylamine / dimethylsulfoxide / 3 h / 20 °C View Scheme

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → 4-({2-[(5-cyanothiazol-2-yl)amino]pyridin-4-yl}methyl)piperazine-1-carboxylic acid methylamide (479611-82-0)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaH / tetrahydrofuran / 0.25 h 1.2: 23.4 g / tetrahydrofuran / 2 h / Heating 2.1: hydrogen fluoride-pyridine / tetrahydrofuran / 1 h 3.1: 15.5 g / phosphorus oxychloride; N,N-dimethylformamide / CH2Cl2 / 4 h 4.1: 82 percent / triethylamine / dimethylsulfoxide / 16 h / 20 °C View Scheme

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → 1-{4-[2-(5-phenyl-thiazol-2-ylamino)-pyridin-4-ylmethyl]-piperazin-1-yl}-ethanone

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaH / tetrahydrofuran / 20 °C 1.2: 79 percent / tetrahydrofuran / 2 h / Heating 2.1: 98 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 1 h / 0 °C 3.1: 90 percent / phosphorus oxychloride; N,N-dimethylformamide / CH2Cl2 / 1.5 h 4.1: dimethylsulfoxide / 16 h / 20 °C View Scheme

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → 4-[2-(5-cyano-thiazol-2-ylamino)-pyridin-4-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaH / tetrahydrofuran / 0.25 h 1.2: 23.4 g / tetrahydrofuran / 2 h / Heating 2.1: hydrogen fluoride-pyridine / tetrahydrofuran / 1 h 3.1: 15.5 g / phosphorus oxychloride; N,N-dimethylformamide / CH2Cl2 / 4 h 4.1: dimethylsulfoxide / 20 °C View Scheme

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → [4-(4-methanesulfonyl-piperazin-1-ylmethyl)-pyridin-2-yl]-(5-phenyl-thiazol-2-yl)-amine

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaH / tetrahydrofuran / 20 °C 1.2: 79 percent / tetrahydrofuran / 2 h / Heating 2.1: 98 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 1 h / 0 °C 3.1: 90 percent / phosphorus oxychloride; N,N-dimethylformamide / CH2Cl2 / 1.5 h 4.1: Et3N / dimethylsulfoxide / 2.5 h / 20 - 45 °C View Scheme

methyl 5,7-dichloro-1-(2-ethoxyethyl)-1H-pyrazolo-[4,3-d]pyrimidine-3-carboxylate (792970-11-7) + 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → methyl 7-{[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]amino}-5-chloro-1-(2-ethoxyethyl)-1H-pyrazolo[4, 3-d]pyrimidine-3-carboxylate

Conditions	Yield
In dichloromethane at 20℃; for 18h;

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine (329794-09-4) → N-(4-(hydroxymethyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine (1377251-36-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C 1.2: 2 h / 65 °C 2.1: potassium carbonate; lithium chloride / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 1 h / 140 °C / microwave irradiation 3.1: hydrogenchloride / methanol / 2 h / 20 °C View Scheme

Upstream product

• 100704-10-7 (2-chloropyridin-4-yl)methanol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 787596-40-1 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloropyridine 
• 105250-17-7 2-amino-4-hydroxymethylpyridine 

Downstream Products

• 329794-10-7 [4-(tert-butyldimethylsilanyloxymethyl)pyridin-2-yl](5-phenylthiazol-2-yl)amine 
• 329794-12-9 (4-chloromethylpyridin-2-yl)(5-phenylthiazol-2-yl)amine 
• 329794-11-8 [2-(5-phenylthiazol-2-ylamino)pyridin-4-yl]methanol 
• 872707-10-3 N-({[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]amino}carbonothioyl)benzamide 

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