4,6-Dichloro-5-methylpyrimidine → (6-Chloro-5-methyl-pyrimidin-4-yl)-[3-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)-propyl]-amine

HRID 1169802ノート

反応式

HRID 1169802 の反応式
[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].[Cl:15][C:16]1[C:21]([CH3:22])=[C:20](Cl)[N:19]=[CH:18][N:17]=1>CC(N(C)C)=O.C(N(C(C)C)CC)(C)C>[Cl: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[CH3:22]

参加物

5

反応物 2

HCID 8188604,6-Dichloro-5-methylpyrimidineHCID 98775993-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)propan-1-amine

生成物 1

HCID 86639119(6-Chloro-5-methyl-pyrimidin-4-yl)-[3-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)-propyl]-amine収率 58%

試薬・触媒・溶媒 2

HCID 31374Dimethylacetamide溶媒HCID 81531Diisopropylethylamine溶媒

実験手順

A mixture of 774.3 mg (4.05 mmoles) of 3-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-ylpropylamine (prepared according to J. Org. Chem, 2004, 69, 1959-1966) and 600 mg (3.68 mmoles) of 4,6-dichloro-5-methyl-pyrimidine in 6 ml of dimethylacetamide and 1.2 ml of diisopropylethylamine is taken to 120° C. for 9 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 Alumina then on silica eluting with a gradient of 100% heptane to 100% ethyl acetate. 680 mg (Yield=58%) of expected product is obtained.

後処理

  1. customThe reaction mixture is evaporated to dryness under reduced pressure (2 kPa)
  2. customThe organic phase is separated
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent evaporated off under reduced pressure (2 kPa)
  5. customThe residue is chromatographed on Alumina

出典と根拠

ORDレコード
ord-84a08765acf14c48a34c53dade264b88
出典データセット
uspto-grants-2010_11
特許番号
US07825119B2

反応ノート

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