Hydrochloric Acid → HCID 68295199, compound

To a solution of 136 (39.5 g, 128 mmol), DCM (100 mL) and MeOH (100 mL) was added 4N solution of HCl in dioxane (160 mL, 640 mmol) and stirred for 18 h. The reaction was concentrated to afford a red oil. The residue was taken up in DCM/7N methanolic NH3 (100 mL, 9:1) and the mixture was sonicated for 5 min. The inorganic salt precipitate was removed by filtration and washed with the same solvent. The filtrate was concentrated to afford a viscous red oil. The crude product was purified by SiO2 chromatography (Biotage 40 M) eluting with DCM/7N methanolic NH3 (7:1). The recovered light brown oil crystallized to form 21.2 g (95%) (S)-2-(5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-ylamino)propan-1-ol (138) as a brown solid: MS m/z (APCI-pos) M+1=209.1.

1. concentrationThe reaction was concentrated
2. customto afford a red oil
3. customthe mixture was sonicated for 5 min
4. customThe inorganic salt precipitate was removed by filtration
5. washwashed with the same solvent
6. concentrationThe filtrate was concentrated
7. customto afford a viscous red oil
8. customThe crude product was purified by SiO2 chromatography (Biotage 40 M)
9. washeluting with DCM/7N methanolic NH3 (7:1)
10. customThe recovered light brown oil crystallized

ORD record

ord-cdec32f79de745579ef31de93c132ef1

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133187B2