Dichloromethane → HCID 58312935, compound

Temperature

-78 °C

A 25 mL round-bottomed flask was charged with methyl 2-chloro-6-methoxypyrimidine-4-carboxylate [sad105-055 crude] (74 mg, 1 equiv.) under argon. 1M DIBAL-H in dichloromethane (0.73 mL, 2 equiv.) was added over 5 min and the reaction mixture was stirred at −78° C. for 45 min. After 0.5 h, LC-MS showed the reaction was complete. The reaction was quenched at −78° C. with methanol (0.5 mL) and then with 10% NH4Cl (2 mL). The solvents were concentrated under reduced pressure and the residue was diluted with 10% NH4Cl (3 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 the crude product 2-chloro-6-methoxypyrimidine-4-carbaldehyde as an orange oil (76 mg, 63 mg theoretical, 121%). LC-MS m/z: 205.0: (M+1+MeOH, hemiacetal with methanol). Some over-reduced alcohol was also observed in the crude (2.17 min, M+1=175). The crude aldehyde was used directly in the next step without further purification.

1. waitAfter 0.5 h
2. customThe reaction was quenched at −78° C. with methanol (0.5 mL)
3. concentrationThe solvents were concentrated under reduced pressure
4. additionthe residue was diluted with 10% NH4Cl (3 mL)
5. extractionThe aqueous layer was extracted with EtOAc (3×10 mL)
6. dry with materialThe combined organic layer was dried over Na2SO4
7. concentrationconcentrated under reduced pressure

ORD record

ord-c810b8daaaae422e9953ce8d0816bba7

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09157077B2