Thymine → Thymine

Reaction equation

[OH-].[CH2:2]([N+:6]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][CH2:4][CH3:5].[NH:19]1[CH:27]=[C:25]([CH3:26])[C:23](=[O:24])[NH:22][C:20]1=[O:21]>CN(C)C=O>[CH2:15]([N+:6]([CH2:2][CH2:3][CH2:4][CH3:5])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:11][CH2:12][CH2:13][CH3:14])[CH2:16][CH2:17][CH3:18].[NH:19]1[CH:27]=[C:25]([CH3:26])[C:23](=[O:24])[NH:22][C:20]1=[O:21]

Participants

Procedure

1.5M Tetra(n-butyl)ammonium hydroxide (4.22 ml., 6.335 mmole) was added to a suspension of thymine (0.913 g., 7.24 mmole) in dimethylformamide (15 ml.). The mixture was stirred for 10 minutes, and the dimethylformamide was removed in vacuo. Additional dimethylformamide (20 ml.) was added to the white residue, and removed in vacuo. This process was repeated four times and the residue was dried under a vacuum (0.1 mm) at 50° C. overnight affording the tetra (n-butyl) ammonium salt of thymine.