Hydrochloric Acid → 2-(chloromethyl)-3H,4H-thieno[3,2-d]pyrimidin-4-one

This compound was prepared by a modification of a method reported for related fused pyrimidine-4(3H)-ones: (1) Shishoo, C. J.; Devani, M. B.; Pathak, U.S.; Ananthan, S.; Bhadti, V. S.; Ullas, G. V.; Jain, K. S.; Rathod, I. S.; Talati, D. S.; Doshi, N. H. J. Heterocyclic Chem. 1984, 21, 375, and (2) Gerecke, M.; Kyburz, E.; Borer, R.; Gassner, W. Heterocycles 1994, 39, 693). An oven-dried 1-L round bottomed flask was charged with chloroacetonitrile (21.86 g, 0.29 mol, 1.3 equiv), methyl 3-aminothiophene-2-carboxylate (35 g, 0.223 mol), and 4 M HCl in 1,4-dioxane (350 mL). The reaction mixture was stirred at room temperature for 1 d. The mixture was evaporated to dryness. The residue was dissolved in water (600 mL) and treated with aqueous 10% sodium bicarbonate to a pH of 8. The resulting slurry was filtered, and the cake washed with water and dried, affording 38.2 g (85%) of the title product. 1H NMR (DMSO-d6) δ 4.58 (s, 2H), 7.42 (d, J=5.3 Hz, 1H), 8.22 (d, J=5.3 Hz, 1H), 12.84 (br s, 1H). LC-MS (APCI) calcd for C7H5ClN2OS: 200.0; Found (M+H+): 201.0 m/z.

1. customThis compound was prepared by a modification of a method
2. customThe mixture was evaporated to dryness
3. dissolutionThe residue was dissolved in water (600 mL)
4. additiontreated with aqueous 10% sodium bicarbonate to a pH of 8
5. filtrationThe resulting slurry was filtered
6. washthe cake washed with water
7. customdried

ORD record

ord-a1a2ca80242f4173b7a8fd395b49693f

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07473790B2