Ethyl bromoacetate → Ethyl {5-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]-2H-tetrazol-2-yl}acetate

HRID 729461Notes

Reaction equation

[NH:1]1[C:5]([C:6]2[CH:7]=[N:8][C:9]([N:12]3[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]3)=[N:10][CH:11]=2)=[N:4][N:3]=[N:2]1.C(N(CC)CC)C.Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>C1COCC1>[OH:18][CH:15]1[CH2:14][CH2:13][N:12]([C:9]2[N:8]=[CH:7][C:6]([C:5]3[N:4]=[N:3][N:2]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:1]=3)=[CH:11][N:10]=2)[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-[5-(1H-tetrazol-5-yl)pyrimidin-2-yl]piperidin-4-ol (550 mg, 2.224 mmol), triethylamine (0.62 mL, 4.45 mmol), ethyl bromoacetate (371 μL, 3.34 mmol) in THF (77.4 mL) was heated at 80° C. for 1 h. The solvent was evaporated, diluted with water (5 mL) and slurried with Et2O (5 mL). The mixture was filtered and washed with water followed by Et2O. The solid was dried under high vacuum to afford the title compound.

Workup

customThe solvent was evaporated
additiondiluted with water (5 mL)
filtrationThe mixture was filtered
washwashed with water
customThe solid was dried under high vacuum

Sources & evidence

ORD record: ord-0fe8d784f3884c9eac8e72e612daa12b
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582633B2

Reaction notes

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