Ethyl orthoformate → 3-(3-Methoxypropyl)-2-thioxanthine

HRID 31062노트

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HRID 31062 반응식
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH2:10][O:11][CH3:12])[C:6](=[S:13])[NH:5][C:4](=[O:14])[C:3]=1[N:15]=O.N[C:18]1C(=O)NC(=S)N(CC2CCCCC2)C=1N.C(OCC)(OCC)OCC>[Pt].O1CCCC1.O.C(O)C>[CH3:12][O:11][CH2:10][CH2:9][CH2:8][N:7]1[C:2]2[N:1]=[CH:18][NH:15][C:3]=2[C:4](=[O:14])[NH:5][C:6]1=[S:13]

참가 물질

8

반응물 3

HCID 31214Ethyl orthoformateHCID 86601053HCID 86601053, 화합물HCID 866010546-amino-1-(3-methoxypropyl)-5-nitroso 2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

생성물 1

HCID 103542623-(3-Methoxypropyl)-2-thioxanthine수율 9%

시약·촉매·용매 4

HCID 23939Platinum촉매HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Platinum on carbon (0.5 g) was added to a solution of the crude 6-amino-1-(3-methoxypropyl)-5-nitroso 2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (1.80 g, 7.38 mmol) in tetrahydrofuran (80 mL) and water (20 mL) and the reaction mixture was hydrogenated at atmospheric pressure for 2 h. The catalyst was filtered off and the pale brown filtrate was co-evaporated with ethanol (250 mL). The resulting brown solid, 1.6 g, was used in the next step without further purification. 5,6-Diamino-1-cyclohexylmethyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (1.6 g, 12.2 mmol) was dissolved in ethanol (10 mL) and triethyl orthoformate (10 mL) and the reaction mixture was refluxed for 2.5 h. The solvents were evaporated off and the resulting brown solid was purified by flash chromatography (heptane/ethyl acetate, 4:1-1:1) to give the title compound (110 mg, 9%).

후처리

  1. filtrationThe catalyst was filtered off
  2. customThe resulting brown solid, 1.6 g, was used in the next step without further purification
  3. customThe solvents were evaporated off
  4. customthe resulting brown solid was purified by flash chromatography (heptane/ethyl acetate, 4:1-1:1)

출처 및 근거

ORD 기록
ord-46148c5d93db4dbaa282d7a294d07ddc
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425560B2

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