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

반응식

HRID 1169802 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 31374Dimethylacetamide용매HCID 81531Diisopropylethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-84a08765acf14c48a34c53dade264b88
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825119B2

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