Tetrabutylammonium Fluoride → (2-chloro-7-cycloheptyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)methanol

Temperature

63 °C

To a suspension of 3-(2-chloro-4-(cycloheptylamino)pyrimidin-5-yl)prop-2-yn-1-ol (8.64 g, 30.9 mmol) in THF (200 mL) was added a solution of TBAF in THF (1 M, 66 mL, 2.1 equiv) and the resulting mixture was heated at 63° C. for 5 h. The reaction mixture was concentrated to remove THF, diluted with EtOAc (350 mL), washed with water (140 mL) and brine (140 mL), dried over Na2SO4, filtered and concentrated. Trituration of the residue using iPrOH, CH2Cl2, and MeCN followed by column chromatography of the mother liquor (EtOAc/heptane 20 to 100%) provided (2-chloro-7-cycloheptyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)methanol (6.24 g) in 72% yield. 1H NMR (400 MHz, CDCl3) δ 8.69 (s, 1H), 6.45 (s, 1H), 4.83 (s, 2H), 4.61 (m, 1H), 2.54 (m, 2H), 1.98-1.86 (m, 4H), 1.73-1.55 (m, 6H); MS m/z 280.4 (M+H)+

1. concentrationThe reaction mixture was concentrated
2. customto remove THF
3. additiondiluted with EtOAc (350 mL)
4. washwashed with water (140 mL) and brine (140 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-36deed8d4ea5452b8df9f5556b3e9c89

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309252B2