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

HRID 732920

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. Harnden 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-dadfa1e4456d4d92a61eb34f1130e36d
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589077B2

Linked notes

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