Thymine → 1-(Methoxymethyl)thymine

Temperature

90 °C

A mixture of thymine (100 g, 0.79 mol), trifluoromethanesulfonic acid (2 mL, 20 mmol) and HMDS (418 mL, 1.98 mol) was heated 16 hours with stirring at 90° C. and briefly at reflux and then distilled in vacuo at 80° C. to remove the excess HMDS. The mixture was treated with trifluoromethanesulfonic acid (1.5 mL, 20 mmol) and then methoxymethyl acetate (88 mL, 0.89 mol) was added at a rate such that the reaction temperature did not exceed 95° C. The mixture was heated 20 minutes at 70° C. and then distilled in vacuo to remove the trimethysilyl acetate formed as byproduct. The reaction mixture was poured into isopropanol (800 mL) and stirred 18 hours. The solids were collected, washed with ethyl acetate and dried to give 1-methoxymethyl-5-methyl-2,4(1H,3H)-pyrimidinedione (116 g, 0.68 mol).

1. temperaturewas heated 16 hours
2. temperaturebriefly at reflux
3. distillationdistilled in vacuo at 80° C.
4. customto remove the excess HMDS
5. customdid not exceed 95° C
6. temperatureThe mixture was heated 20 minutes at 70° C.
7. distillationdistilled in vacuo
8. customto remove the trimethysilyl acetate
9. customformed as byproduct
10. stirringstirred 18 hours
11. customThe solids were collected
12. washwashed with ethyl acetate
13. customdried

ORD record

ord-0227304d256a461cae542b436aaaed11

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05859014