2-Bromopyrimidine → HCID 22027827, compound

HRID 1828043Notes

Reaction equation

HRID 1828043 reaction equation
[C:1]([O:5][C:6]([O:8][NH:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.Br[C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1>C(#N)C>[C:1]([O:5][C:6]([O:8][NH:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:28]2[N:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[CH2:14][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 783452-BromopyrimidineHCID 81531DiisopropylethylamineHCID 22027796HCID 22027796, compound

Product 1

HCID 22027827HCID 22027827, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-t-butoxycarbonyloxy 2-(piperidin-4-yl)-ethylamine (prepared per Method K′ above), DIEA (0.75 mL) and 2-bromopyrimidine (204 mg) (Aldrich) in acetonitrile (5 mL) were heated under reflux overnight. The solvent was removed under reduced pressure and the black liquid was subjected to a column chromatography, eluted with 1:1 EtOAc/hexanes, to give pure N-t-butoxycarbonyloxy 2-[1-(pyrimidin-2-yl)piperidin-4-yl]-ethylamine as a pale yellow oil. 1H NMR (CDCl3) δ=8.21 (d, J=5.1 Hz, 2H), 6.36 (t, J=5.1 Hz, 1H), 4.64 (d, J=13.8 Hz, 2H), 3.14–3.07 (m, 2H), 2.76 (dt, J=2.7, 13.2 Hz, 1H), 1.69 (d, J=13.8 Hz, 1H), 1.57–1.30 (m, 11H), 1.20–1.03 (m, 3H);

Workup

  1. temperaturewere heated
  2. temperatureunder reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. washeluted with 1:1 EtOAc/hexanes

Sources & evidence

ORD record
ord-dc0327199a8547bb8d8236b44b2b001d
Source dataset
uspto-grants-2006_06
Patent number
US07056937B2

Reaction notes

Loading…