2-Chloro-1,1-dimethoxyethane → 1H-Pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione, 1,3-dimethyl-

To a stirred solution of chloroacetaldehyde dimethyl acetal (26.0 g, 208.717 mmol) in water (60 mL) concentrated hydrochloric acid (4 mL) was added at room temperature and the reaction mixture was stirred at near boiling until a homogeneous solution was obtained. Solution of sodium acetate (8.0 g, 97.525 mmol) was then added. The resulting mixture was then added to a stirred solution consisting of 6-amino-1,3-dimethyl uracil (20.0 g, 128.907 mmol) and sodium acetate (16.0 g, 195.051) in water (100 mL) at 90° C. All solid material was dissolved, then after 10 min. a precipitate was started to form. The reaction mixture was stirred for another 30 min. at the same temperature. The reaction mixture was cooled to room temperature and solid obtained was filtered, washed with water (2×250 mL) and then acetone (2×150 mL). The solid obtained was dried in oven at 65° C. to obtain 7.81 g of the product as an off-white solid; 1H NMR (δ ppm, 300 MHz, DMSO-d6) 3.20 (s, 3H), 3.42 (s, 3H), 6.35 (s, 1H), 6.77 (s, 1H), 11.71 (br s, 1H); APCI-MS (m/z) 180.25 (M+H)+.

1. customwas obtained
2. additionThe resulting mixture was then added to a stirred solution
3. dissolutionAll solid material was dissolved
4. customto form
5. stirringThe reaction mixture was stirred for another 30 min. at the same temperature
6. customsolid obtained
7. filtrationwas filtered
8. washwashed with water (2×250 mL)
9. customThe solid obtained
10. customwas dried in oven at 65° C.

ORD-Eintrag

ord-4569ae6164754a85b92e57d496a8effd

Quelldatensatz

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08623880B2