1-Butanol → HCID 86664565, compound

HRID 1426891Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]2[N:3]=1.[F:16][C:17]1[CH:18]=[C:19]([C@H:25]2[CH2:29][CH2:28][CH2:27][NH:26]2)[C:20]([O:23][CH3:24])=[N:21][CH:22]=1.CCN(C(C)C)C(C)C.C(O)CCC>CCOC(C)=O>[F:16][C:17]1[CH:18]=[C:19]([C@H:25]2[CH2:29][CH2:28][CH2:27][N:26]2[C:2]2[CH:7]=[CH:6][N:5]3[N:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]3[N:3]=2)[C:20]([O:23][CH3:24])=[N:21][CH:22]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (0.75 g, 3.32 mmol), (R)-5-fluoro-2-methoxy-3-(pyrrolidin-2-yl)pyridine (Preparation A, 0.984 g, 3.66 mmol), DIEA (2.32 mL, 13.3 mmol) and n-butanol (1.11 mL) was sealed in a pressure tube and heated at 90° C. for 48 hours. The reaction mixture was diluted with EtOAc and washed with water, brine and sat NaHCO3. The organic layer was dried (MgSO4), filtered and concentrated to afford a dark orange oil. The crude material was purified by silica column chromatography eluting with 50-80% EtOAc/hexanes to afford (R)-ethyl 5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (0.72 g, 56.2% yield) as a yellow foamy solid. MS (apci) m/z=386.0 (M+H).

Workup

customwas sealed in a pressure tube
washwashed with water, brine
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customto afford a dark orange oil
customThe crude material was purified by silica column chromatography
washeluting with 50-80% EtOAc/hexanes

Sources & evidence

ORD record: ord-26bbd5d5cb074157b34d9b92b87e42e0
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933084B2

Reaction notes

Loading…