Uracil → 1-[2-(2,2-Dimethyl-1,3-dioxan-5-yl)ethyl]uracil

HRID 908527

Reaction equation

[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:16][CH2:17][CH:18]1[CH2:23][O:22][C:21]([CH3:25])([CH3:24])[O:20][CH2:19]1>CN(C=O)C>[CH3:24][C:21]1([CH3:25])[O:22][CH2:23][CH:18]([CH2:17][CH2:16][N:1]2[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]2=[O:3])[CH2:19][O:20]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of uracil (88.5 g, 0.79 mol) in dry DMF (250 mL) was added cesium carbonate (171 g, 0.527 mol) at RT and stirred at the same temperature for 30 min. To the above reaction mixture was added a solution of compound 33 (117 g, 0.527 mol) in dry DMF (250 mL) over a period of 30 min and heated at 50° C. for 24 h. The reaction mixture was filtered, filtrate concentrated under vacuum and crude purified by column chromatography over silica gel (3% methanol in chloroform) to give the title compound (60 g, 45%). TLC: Chloroform/Methanol, 4:1, Rf=0.3

Workup

filtrationThe reaction mixture was filtered
concentrationfiltrate concentrated under vacuum and crude
custompurified by column chromatography over silica gel (3% methanol in chloroform)

Sources & evidence

ORD record: ord-b0c9446791bd4fca8105e0ad0917d13a
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017620B2

Linked notes

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