Trimethyl orthoformate → (S)-3-methyl-4-(6-((4-methylpiperazin-1-yl)methyl)-2-(pyrimidin-5-yl)thieno[3,2-d]pyrimidin-4-yl)morpholine

Following General Procedure D, (S)-2-chloro-4-(3-methylmorpholino)thieno[3,2-d]pyrimidine-6-carbaldehyde (100 mg, 0.34 mmol), HOAc (25 mg), NaBH(OAc)3 (80 mg, 0.37 mmol), N-methylpiperazine (41 mg, 0.40 mmol), 1,2-dichloroethane (1.0 mL), trimethylorthoformate were reacted at room temperature. The crude product was used in the next step without purification. MS (Q1) 382 (M)+. Following General Procedure A, crude product from above, pyrimidine-5-boronic acid (27 mg), Pd(PPh3)4 (20 mg), MeCN (1 mL) and 1M KOAc in H2O (1 mL) were irradiated at 150° C. for 30 min. The reaction mixture was diluted with CH2Cl2, and filtered. The filtrate was concentrated to give crude 422 which was purified by reverse phase HPLC. (14 mg) MS (Q1) 426 (M)+

1. customwere reacted at room temperature
2. customThe crude product was used in the next step without purification
3. customwere irradiated at 150° C. for 30 min
4. additionThe reaction mixture was diluted with CH2Cl2
5. filtrationfiltered
6. concentrationThe filtrate was concentrated
7. customto give crude 422 which
8. customwas purified by reverse phase HPLC

ORD 기록

ord-6f722b48dad84a3c870768ce28aaf007

출처 데이터셋

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08993563B2