Triphenylphosphine → Ethyl (5-{2-[4-(5-bromo-2-chlorophenoxy)piperidin-1-yl]pyrimidin-5-yl}-2H-tetrazol-2-yl)acetate

HRID 729462Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]3[N:15]=[N:16][N:17]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:18]=3)=[CH:10][N:9]=2)[CH2:4][CH2:3]1.[Br:25][C:26]1[CH:27]=[CH:28][C:29]([Cl:33])=[C:30](O)[CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Br:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:33])=[C:28]([CH:27]=1)[O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]2[N:9]=[CH:10][C:11]([C:14]3[N:15]=[N:16][N:17]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:18]=3)=[CH:12][N:13]=2)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl {5-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]-2H-tetrazol-2-yl}acetate (44 mg, 0.132 mmol), 5-bromo-2-chlorophenol (32.9 mg, 0.158 mmol) and triphenylphosphine (45 mg, 0.172 mmol) in THF (660 μL) was added diethyl azodicarboxylate (27.2 μL, 0.172 mmol). The mixture was heated at 50° C. for 4 h. The solvent was evaporated and the crude product was purified by Combiflash chromatography (SiO2-12 g, gradient elution of 10-50% EtOAc/hexanes over 30 min) to afford the title product as a solid. MS: m/z 422, 424 (MH+).

Workup

customThe solvent was evaporated
customthe crude product was purified by Combiflash chromatography (SiO2-12 g, gradient elution of 10-50% EtOAc/hexanes over 30 min)

Sources & evidence

ORD record: ord-a7962fb257c24fb8b5bda1e1f4bbaf25
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582633B2

Reaction notes

Loading…