3-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)propan-1-amine → (6-Bromo-5-ethyl-pyrimidin-4-yl)-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-propyl]-amine
Reaction equation
[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][NH2:14].[Br:15][C:16]1[C:21]([CH2:22][CH3:23])=[C:20](Br)[N:19]=[CH:18][N:17]=1>CC(N(C)C)=O.C(N(C(C)C)CC)(C)C>[Br:15][C:16]1[N:17]=[CH:18][N:19]=[C:20]([NH:14][CH2:13][CH2:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[CH2:6][CH2:7][CH2:8][NH:9][C:10]=3[N:1]=2)[C:21]=1[CH2:22][CH3:23]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 0.20 g (1 mmole) of 3-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-ylpropylamine [prepared according to J. Org. Chem. 2004, 69, (1959-1966)] and 0.30 g (1.1 mmoles) of 4,6-dibromo-5-ethyl-pyrimidine in 20 ml of dimethylacetamide and 1 ml of diisopropylethylamine is taken to 120° C. for 6 hours. The reaction mixture is evaporated to dryness under reduced pressure (2 kPa) and the residue is taken up in ethyl acetate, water and a saturated solution of sodium bicarbonate. The organic phase is separated, dried over magnesium sulphate and the solvent evaporated off under reduced pressure (2 kPa). The residue is chromatographed on silica gel eluting with a gradient of 100% heptane to 100% ethyl acetate. 0.21 g of expected product is obtained in the form of a yellow oil.
Workup
- customThe reaction mixture is evaporated to dryness under reduced pressure (2 kPa)
- customThe organic phase is separated
- dry with materialdried over magnesium sulphate
- customthe solvent evaporated off under reduced pressure (2 kPa)
- customThe residue is chromatographed on silica gel eluting with a gradient of 100% heptane to 100% ethyl acetate
Sources & evidence
- ORD record
- ord-332a7d1ac396496bbe7542956325d210
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765766B2
Reaction notes
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