5,6,7,8-TETRAHYDRO-6-METHYL-1,6-NAPHTHYRIDIN-3-AMINE synthesis
- Product Name:5,6,7,8-TETRAHYDRO-6-METHYL-1,6-NAPHTHYRIDIN-3-AMINE
- CAS Number:216966-37-9
- Molecular formula:C9H13N3
- Molecular Weight:163.22
123792-64-3
216966-37-9
General procedure for the synthesis of 3-amino-5,6,7,8-tetrahydro-6-methyl-1,6-naphthyridine from 6-methyl-3-nitro-5,6,7,8-tetrahydro-6-methyl-1,6-naphthyridine: To a mixture of ethanol (35 mL) and 2-methyltetrahydrofuran (35 mL) of intermediate 128 (1.50 g, 7.76 mmol) was added palladium/carbon catalyst ( 10 wt.%) (826.24 mg, 0.77 mmol) and the reaction mixture was stirred under hydrogen atmosphere for 2 hours. After completion of the reaction, the mixture was filtered through a diatomaceous earth pad and the filter cake was washed with ethanol. The filtrate was concentrated under reduced pressure to give 1.33 g of Intermediate 129, which crystallized on standing (quantitative yield, 95% purity based on 1H NMR analysis, yellow oily).
123792-64-3
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216966-37-9
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Yield: 100%
Reaction Conditions:
with palladium 10% on activated carbon;hydrogen in 2-methyltetrahydrofuran;ethanol for 2 h;
Steps:
A18a Preparation of intermediate 129:
To a solution of intermediate 128 (1.50 g, 7.76 mmol) in EtOH (35 mL) and Me-THF (35 mL) was added Pd/C (10 wt. %) (826.24 mg, 0.77 mmol) and the mixture was stirred under H2 atmosphere for 2 h. The mixture was filtered over a pad of celite and the cake was washed with EtOH. The filtrate was evaporated in vacuo to give 1.33 g of intermediate 129 which crystallized upon standing (quant. yield, 95% purity based on 1H NMR, yellow oil).
References:
JANSSEN PHARMACEUTICA NV;STANSFIELD, Ian;QUEROLLE, Olivier, Alexis, Georges;LIGNY, Yannick, Aimé, Eddy;GROSS, Gerhard, Max;JACOBY, Edgar;MEERPOEL, Lieven;GREEN, Simon, Richard;HYND, George;KULAGOWSKI, Janusz, Jozef;MACLEOD, Calum;MANN, Samuel, Edward WO2018/2219, 2018, A1 Location in patent:Page/Page column 290; 291
1445-73-4
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$15.00/25g
216966-37-9
50 suppliers
$77.00/100mg