Hydrochloric Acid → 5-Hydrazinyl-2,4-dimethoxypyrimidine

Temperature

0 °C

Di-tert-butyl 1-(2,4-dimethoxypyrimidin-5-yl)hydrazine-1,2-dicarboxylate (Step 46.7) (453 g, 1.223 mol) was dissolved in MeOH (2.5 L) and cooled down to 0° C. HCl 4N in gioxane (2.5 L, mol) was added and the resulting mixture was stirred at RT overnight. The reaction was concentrated under reduced pressure, NH3 4 N (2 L) was added, the resulting mixture was stirred for 1 hr and concentrated under reduced pressure. CH2Cl2 (2 L) was added, the suspension was filtrated off and the filtrate was concentrated under reduced pressure. The crude product was stirred with Et2O (2 L) at 0° C. for 30 min. The resulting suspension was filtrated off and dried to afford the title product (150 g, 864 mmol, 70% yield) as light beige solid. tR: 0.32 min (LC-MS 1); ESI-MS: 171 [M+H]+ (LC-MS 1).

1. concentrationThe reaction was concentrated under reduced pressure, NH3 4 N (2 L)
2. additionwas added
3. stirringthe resulting mixture was stirred for 1 hr
4. concentrationconcentrated under reduced pressure
5. additionCH2Cl2 (2 L) was added
6. filtrationthe suspension was filtrated off
7. concentrationthe filtrate was concentrated under reduced pressure
8. stirringThe crude product was stirred with Et2O (2 L) at 0° C. for 30 min
9. filtrationThe resulting suspension was filtrated off
10. customdried

ORD record

ord-8d3fbf98053a4362a3b7c8424c12bd79

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08975417B2