Chloroform → HCID 67252547, compound

Temperature

60 °C

4-Chloro-5-(5-cyclopropyl[1,3,4]oxadiazol-2-yl)-2-methylthiopyrimidine (13 mg, 0.050 mmol) [Compound (AC) in which Q is a chlorine atom, R2B is methylthio, and —X—Y—Z— is —O—C(c-C3H5)═N—] obtained in Reference Example 3 was dissolved in THF (0.50 mL), then triethylamine (0.007 mL) and a chloroform solution (1.0 mol/L, 0.20 mL) of R1—H [wherein R1 has the same definition as described above: Compound (B)] were added thereto, followed by stirring at 60° C. for 12 hours with hermetic sealing. After completion of the reaction was confirmed by thin-layer chromatography, the reaction mixture was concentrated and dried. The residue was dissolved in chloroform/methanol (chloroform:methanol=3:1, 0.50 mL), then benzoyl chloride polymer-bound [about 2.5 mmol/g, 46 mg, Canadian Journal of Chemistry, vol. 55, p. 3351 (1977)], and poly(4-vinylpyridine) (46 mg) were added thereto, followed by further stirring at room temperature for 12 hours. The resin was filtered off from the reaction mixture, and the filtrate was concentrated and dried to give 4-amino-5-(5-cyclopropyl[1,3,4]oxadiazol-2-yl)-2-methylthiopyrimidine [Compound (AD) in which —X—Y—Z— is —O—C(c-C3H5)═N—].

1. customobtained in Reference Example 3
2. additionwere added
3. concentrationthe reaction mixture was concentrated
4. customdried
5. dissolutionThe residue was dissolved in chloroform/methanol (chloroform:methanol=3:1, 0.50 mL)
6. addition3351 (1977)], and poly(4-vinylpyridine) (46 mg) were added
7. stirringby further stirring at room temperature for 12 hours
8. filtrationThe resin was filtered off from the reaction mixture
9. concentrationthe filtrate was concentrated
10. customdried

ORD record

ord-3a8ad93f5ddc4d5ba414715dcf920143

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07956060B2