Trifluoroacetic acid → HCID 58739080, compound

HRID 720293Notes

Reaction equation

HRID 720293 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:22]2[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24][CH2:23]2)[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[O:12]CC1C=CC=CC=1)=[O:5])[CH3:2].[F:29][C:30]([F:35])([F:34])[C:31](O)=[O:32]>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:22]2[CH2:27][CH2:26][CH:25]([O:28][C:31](=[O:32])[C:30]([F:35])([F:34])[F:29])[CH2:24][CH2:23]2)[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[OH:12])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21060062HCID 21060062, compound

Product 1

HCID 58739080HCID 58739080, compound

Procedure

5-Benzyloxy-2-(4-hydroxypiperidin-1-yl)-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid ethyl ester (0.760 g, 1.96 mmol) was treated with trifluroacetic acid (20 mL) at ambient temperature. After 10 h, the reaction mixture was concentrated and purified on silica gel column using 2–5% MeOH/CH2Cl2 to afford desired product as a brown paste (0.650 g, 84%). 1H NMR (500 MHz, CDCl3) δ: 10.02 (br s, 1H), 5.23–5.19 (m, 1H), 4.44 (q, J=7.0 Hz, 2H), 3.57 (s, 3H), 3.36–3.31 (m, 2H), 3.15–3.10 (m, 2H), 2.17–2.11 (m, 2H), 2.02–1.95 (m, 2H), 1.42 (t, J=7.0 Hz, 3H). LRMS (M+H) calcd for C15H19F3N3O6: 394.32. found: 394.09

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified on silica gel column

Sources & evidence

ORD record
ord-60b9a6b894e4486d9f6a88b5ba3dcfb5
Source dataset
uspto-grants-2006_11
Patent number
US07135467B2

Reaction notes

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