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

HRID 31062ノート

反応式

HRID 31062 の反応式
[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]

参加物

8

反応物 3

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

生成物 1

HCID 103542623-(3-Methoxypropyl)-2-thioxanthine収率 9%

試薬・触媒・溶媒 4

HCID 23939Platinum触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-46148c5d93db4dbaa282d7a294d07ddc
出典データセット
uspto-grants-2008_09
特許番号
US07425560B2

反応ノート

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