2-Amino-4-(benzyloxy)pyridine synthesis
- Product Name:2-Amino-4-(benzyloxy)pyridine
- CAS Number:85333-26-2
- Molecular formula:C12H12N2O
- Molecular Weight:200.24
182556-72-5
85333-26-2
Step A: Preparation of 4-(benzyloxy)pyridin-2-amine: 4-(benzyloxy)-2-chloropyridine (1.10 g, 5.01 mmol), Pd2dba3 (46 mg, 0.05 mmol), and 2-(dicyclohexylphosphino)-2',4',6'-tripropyl-1,1 '-biphenyl (57 mg, 0.120 mmol) were dissolved in THF (10 mL) in THF (10 mL) and a 1.0 M solution of ammonia in THF (6 mL) was added. The mixture was heated to 65 °C for 30 min of reaction and then cooled to room temperature. The reaction mixture was concentrated by a silica gel column and eluted with a 20:1 solvent mixture of ethyl acetate/methanol to give a light golden solid product (0.97 g, 96% yield).
182556-72-5
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85333-26-2
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Yield:85333-26-2 96%
Reaction Conditions:
with lithium hexamethyldisilazane;tris-(dibenzylideneacetone)dipalladium(0);2-(dicyclohexylphosphino)-2',4',6'-tri-1-propyl-1,1'-biphenyl in tetrahydrofuran at 65; for 0.5 h;
Steps:
10.A
Example 10 ; [Show Image] Synthesis of N4-(4-(H-imidazo[1,2-a]pyridin-7-yloxy)-3-methylphenyl)-N6-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)quinazoline-4,6-diamine Step A: Preparation of 4-(benzyloxy)pyridin-2-amine: To a mixture of 4-(benzyloxy)-2-chloropyridine (1.10 g, 5.01 mmol), Pd2dba3 (46 mg, 0.05 mmol) and 2-(dicyclohexylphosphino)-2',4',6'-tri-propyl-1,1'-biphenyl (57 mg, 0.120 mmol) in THF (10 mL) was added LHMDS (6 mL of 1.0 M solution). After heating to 65 °C for 30 minutes, the mixture was cooled to room temperature and concentrated onto silica gel. The product was eluted with 20:1 ethyl acetate/methanol to isolate a pale gold solid (0.97 g, 96%).
References:
EP2090575,2009,A1 Location in patent:Page/Page column 54-55
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85333-26-2
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85333-26-2
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