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329794-09-4

Basic Information
CAS No.: 329794-09-4
Name: 4-(TERT-BUTYL-DIMETHYL-SILANYLOXYMETHYL)-PYRIDIN-2-YLAMINE
Article Data: 12
Molecular Structure:
Molecular Structure of 329794-09-4 (4-(TERT-BUTYL-DIMETHYL-SILANYLOXYMETHYL)-PYRIDIN-2-YLAMINE)
Formula: C12H22 N2 O Si
Molecular Weight: 238.405
Synonyms: 2-Amino-4-(tert-butyldimethylsilyloxymethyl)pyridine;4-(tert-Butyldimethylsilanyloxymethyl)pyridin-2-ylamine;4-[[(tert-Butyldimethylsilyl)oxy]methyl]pyridin-2-amine
Density: 0.983 g/cm3
Melting Point: 109.2-109.3°C
Boiling Point: 320.6 ºC at 760 mmHg
Flash Point: 147.7 ºC
Hazard Symbols:
PSA: 48.14000
LogP: 3.76680
Synthetic route
18162-48-6

tert-butyldimethylsilyl chloride

105250-17-7

2-amino-4-hydroxymethylpyridine

329794-09-4

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine

Conditions
ConditionsYield
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

329794-09-4

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine

Conditions
ConditionsYield
With hydroxylamine In methanol at 20℃; for 18h;17.89 g
100704-10-7

(2-chloropyridin-4-yl)methanol

329794-09-4

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine

Conditions
ConditionsYield
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
18162-48-6

tert-butyldimethylsilyl chloride

MeHal

MeHal

329794-09-4

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine

Conditions
ConditionsYield
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
787596-40-1

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloropyridine

329794-09-4

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine

Conditions
ConditionsYield
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
1759-53-1

cyclopropanecarboxylic acid

329794-09-4

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine

N-(4-(((tert-butyldimethylsilyl)oxy)methyl)pyridin-2-yl)cyclopropanecarboxamide

Conditions
ConditionsYield
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%
329794-40-3

2-chloro-5-phenyl-thiazole

329794-09-4

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine

329794-10-7

[4-(tert-butyldimethylsilanyloxymethyl)pyridin-2-yl](5-phenylthiazol-2-yl)amine

Conditions
ConditionsYield
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%
532-55-8

Benzoyl isothiocyanate

329794-09-4

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine

872707-10-3

N-({[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]amino}carbonothioyl)benzamide

Conditions
ConditionsYield
In toluene at 85℃; for 12h; Heating / reflux;79%
In toluene at 85℃; for 12h;79%
In toluene at 85℃; for 12h;79%
24424-99-5

di-tert-butyl dicarbonate

329794-09-4

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine

864460-81-1

tert-butyl (4-(((tert-butyldimethylsilyl)oxy)methyl)pyridin-2-yl)carbamate

Conditions
ConditionsYield
With pyridine In ethyl acetate; tert-butyl alcohol at 20℃;62%
80945-86-4

6-bromo-2-chloro-benzothiazole

329794-09-4

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine

1377264-31-7

6-bromo-N-(4-(((tert-butyldimethylsilyl)oxy)methyl)pyridin-2-yl)benzo[d]thiazol-2-amine

Conditions
ConditionsYield
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%
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