Dichloromethane → HCID 58312971, Verbindung

A 25 mL round bottomed flask was charged with methyl 2-chloro-6-(2-methoxyethoxy)pyrimidine-4-carboxylate [SAD105-047F1] (45 mg, 1 equiv.) and CH2Cl2 (1 mL). 1 M DIBAL-H (0.2 mL, 1.1 equiv.) was added at −78° C. over 2 min under argon. The reaction mixture was stirred for 3 h at −78° C. but the LC-MS still showed a lot of starting material. Additional 1 M DIBAL-H (0.27 mL, 1.4 equiv.) was added at −78° C. over 2 min under argon and after 0.5 h LC-MS showed no more starting material but mostly 1 peak at 1.20 min (M+1=217, M+l+MeOH=249). The reaction mixture was quenched with MeOH (0.5 mL) and then with 10% NH4Cl (1 mL). The reaction mixture was warmed to RT and then the solvent was concentrated under reduced pressure. The residue was diluted with 10% NH4Cl (4 mL). The aqueous layer was extracted with EtOAc (3×10 mL). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure to provide 41.9 mg of the crude 2-chloro-6-(2-methoxyethoxy)pyrimidine-4-carbaldehyde as a yellow oil which was used in the next step without further purification, (H NMR δ: 9.91 (s, 1H); 7.23 (s, 1H); 4.59-4.64 (m, 2H), 3.7-3.8 (m, 2H); 3.44 (s, 3H).

1. customat 1.20 min
2. customThe reaction mixture was quenched with MeOH (0.5 mL)
3. temperatureThe reaction mixture was warmed to RT
4. concentrationthe solvent was concentrated under reduced pressure
5. additionThe residue was diluted with 10% NH4Cl (4 mL)
6. extractionThe aqueous layer was extracted with EtOAc (3×10 mL)
7. dry with materialThe combined organic layer was dried over Na2SO4
8. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-cacdda6639d44e45b3715d290d928098

Quelldatensatz

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09157077B2