Tert-butyl 4-hydroxypiperidine-1-carboxylate → 5-(1-Tert-butoxycarbonylpiperidin-4-yloxy)-3,4-dihydroquinazolin-4-one

HRID 641760Notes

Reaction equation

HRID 641760 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.F[C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[C:18](=[O:26])[NH:19][CH:20]=[N:21]2>>[C:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:2]([O:1][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[C:18](=[O:26])[NH:19][CH:20]=[N:21]3)[CH2:7][CH2:6]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 1354959305-Fluoroquinazolin-4-ol

Product 1

HCID 1355106735-(1-Tert-butoxycarbonylpiperidin-4-yloxy)-3,4-dihydroquinazolin-4-oneYield 103%

Procedure

Thus, tert-butyl 4-hydroxypiperidine-1-carboxylate (0.33 g) was reacted with 5-fluoro-3,4-dihydroquinazolin-4-one (0.18 g) to give 5-(1-tert-butoxycarbonylpiperidin-4-yloxy)-3,4-dihydroquinazolin-4-one (0.39 g); NMR Spectrum: (CDCl3) 1.5 (s, 9H), 1.9-2.0 (m, 4H), 3.52 (m, 2H), 3.7 (m, 2H), 4.72 (m, 1H), 6.95 (d, 1H), 7.32 (d, 1H), 7.65 (m, 1H), 7.95 (s, 1H), 10.22 (br s, 1H); Mass Spectrum: M+H+ 346;

Sources & evidence

ORD record
ord-73e82d46979f4ce4adbf09b359305a3d
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Reaction notes

Loading…