1,6-NAPHTHYRIDIN-2-AMINE synthesis

5synthesis methods

Product Name:1,6-NAPHTHYRIDIN-2-AMINE
CAS Number:17965-81-0
Molecular formula:C8H7N3
Molecular Weight:145.16

tert-butyl 1,6-naphthyridin-2-ylcarbamate

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17965-81-0
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Yield:17965-81-0 99%

Reaction Conditions:

Stage #1: tert-butyl (1,6-naphthyridin-2-yl)carbamatewith trifluoroacetic acid in dichloromethane; for 0.5 h;
Stage #2: with sodium hydrogencarbonate in water;

Steps:

68

A 50% TFA/DCM mixture (10 mL) was added to tert-butyl 1,6-naphthyridin-2-ylcarbamate (2.7 g, 11.0 mmol) from the above step. After 30 minutes, the reaction mixture was concentrated and diluted with 30 mL of water. A saturated NaHCO₃solution (15 mL) was added, and the reaction mixture was extracted twice with 50 mL of EtOAc. The organic layers were combined, concentrated, and purified by chromatography through a Redi-Sep pre-packed silica gel column (120 g), eluting with a gradient 0-15% MeOH/DCM to give 1,6-naphthyridin-2-amine (1.6 g, 99% yield). MS m/z: 145 (M+1). ¹H NMR (400 MHz, (CD₃OD)): δ ppm 6.93 (d, J=9.00 Hz, 1H), 7.41 (d, J=6.06 Hz, 1H), 8.05 (d, J=9.00 Hz, 1H), 8.37 (d, J=5.87 Hz, 1H), 8.83 (s, 1H).

References:

US2007/173506,2007,A1 Location in patent:Page/Page column 57

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23616-33-3
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17965-81-0
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References

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17965-81-0
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References

253-72-5
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17965-81-0
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References

1,6-Naphthyridin-2-amine, N-(dimethyl-λ4-sulfanylidene)-

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References