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

HRID 1516769Notes

Reaction equation

Br[CH2:2][CH2:3][CH:4]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[O:6][CH2:5]1.[NH:12]1[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]1=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:10][C:7]1([CH3:11])[O:8][CH2:9][CH:4]([CH2:3][CH2:2][N:12]2[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]2=[O:14])[CH2:5][O:6]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-(2-bromoethyl)-2,2-dimethyl-1,3-dioxane (15) (M. R. Hamden et al, J. Med. Chem., 30, 1636, 1987) (12.0 gm, 53.81 mmol) in dry DMF (150 ml) were added uracil (7.0 gm, 62.4 mmol) and potassium carbonate (14.0 gm). The reaction mixture was stirred at 25° C. for 5 days. The resulting solution was filtered and the solvent removed. The residue obtained was purified by column chromatography on silica gel eluting with chloroform-methanol (90:10, v/v) to afford 17 (4.0 gm, 25.2%).

Workup

filtrationThe resulting solution was filtered
customthe solvent removed
customThe residue obtained
customwas purified by column chromatography on silica gel eluting with chloroform-methanol (90:10

Sources & evidence

ORD record: ord-04e91614e5444441abb1087c15460186
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227594B2

Reaction notes

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