Ethanol → 3-(3-Methoxypropyl)-2-thioxanthine

HRID 883550Notes

Reaction equation

HRID 883550 reaction equation
[NH2:1][C:2]1[C:3](=[O:17])[NH:4][C:5](=[S:16])[N:6]([CH2:9][CH:10]2CCCC[CH2:11]2)[C:7]=1[NH2:8].[CH:18](OCC)(OCC)[O:19]CC.[CH2:28](O)C>>[CH3:18][O:19][CH2:11][CH2:10][CH2:9][N:6]1[C:7]2[N:8]=[CH:28][NH:1][C:2]=2[C:3](=[O:17])[NH:4][C:5]1=[S:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 31214Ethyl orthoformateHCID 86601053HCID 86601053, compound

Product 1

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

Procedure

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%).

Workup

  1. customThe solvents were evaporated off
  2. customthe resulting brown solid was purified by flash chromatography (heptane/ethyl acetate, 4:1-1:1)

Sources & evidence

ORD record
ord-bab2a1909e9c4c839b29f24efb4f6a4e
Source dataset
uspto-grants-2012_08
Patent number
US08236951B2

Reaction notes

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