Acetic Acid → 7-Methylthieno[3,2-d]pyrimidine-2,4(1H,3H)-dione

温度

10 °C

Methyl 3-amino-4-methylthiophene-2-carboxylate IX (100 g, 0.584 mol) and acetic acid (750 mL, 13.1 mol) were stirred for 5 min to obtain a clear solution. A solution of potassium cyanate (56.8 g, 0.70 mol) in water (120 mL) was slowly added over 20 min, and the mixture was stirred for 1.5 h. Additional potassium cyanate (56.8 g, 0.70 mol) in water (120 mL) was slowly added over 20 min and the mixture was stirred for 2 h. Water (600 mL) was added and the mixture was cooled to 10° C. and stirred for 2 h. The solid was collected by filtration and washed with cold water (250 mL). The solid was then stirred for 12 h in a solution of sodium hydroxide (79.4 g, 1.99 mol) in water (1.4 L). The pH was adjusted to 6-7 by slow addition of aqueous concentrated hydrochloric acid solution (35 wt %, 110 mL) and was then stirred for 5 min. The resulting solid was collected by filtration, washed with water (2×250 mL) and dried under reduced pressure at 50° C. for 24 h to afford 7-methylthieno[3,2-d]pyrimidine-2,4(1H,3H)-dione VIII as an off-white solid (89.6 g, 84% yield). 1H NMR (500 MHz, DMSO-d6) δ 7.68 (s, 1H), 2.20 (s, 3H); LCMS (ESI pos) m/z [M+H] 183.

1. customto obtain a clear solution
2. stirringthe mixture was stirred for 2 h
3. stirringstirred for 2 h
4. filtrationThe solid was collected by filtration
5. washwashed with cold water (250 mL)
6. stirringwas then stirred for 5 min
7. filtrationThe resulting solid was collected by filtration
8. washwashed with water (2×250 mL)
9. customdried under reduced pressure at 50° C. for 24 h

ORDレコード

ord-34b37c6dd553496a9e450fcfa70b76f9

出典データセット

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08895729B2