5-Bromo-2-chloropyrimidine → HCID 71260769, compound

HRID 1054489Notes

Reaction equation

HRID 1054489 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:9][C@H:10]1[CH2:14][CH2:13][CH2:12][NH:11]1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:12][CH2:13][CH2:14][C@@H:10]2[CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6066655-Bromo-2-chloropyrimidineHCID 6999702(2S)-2-methylpyrrolidine

Product 1

HCID 71260769HCID 71260769, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid 5-bromo-2-chloropyrimidine (27.5 g, 142 mmol) was added in three portions to a 500 mL flask containing (S)-2-methylpyrrolidine (20.24 ml, 213 mmol) stirred at room temperature. After 1 hr the resulting solids were dissolved in warm DCM, washed with water, brine, dried over MgSO4 and concentrated onto silica in vacuo. Column purified by silica gel chromatography to afford white crystalline solids (30.7 g, 89%), ESI-MS (EI+, m/z): 241.02, 1H NMR (Chloroform-d) δ: 8.31 (d, J=5.0 Hz, 2H), 4.33-4.14 (m, 1H), 3.61 (tt, J=7.6, 3.0 Hz, 1H), 3.56-3.41 (m, 1H), 2.23-1.88 (m, 3H), 1.88-1.63 (m, 1H), 1.25 (t, J=5.5 Hz, 3H)

Workup

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated onto silica in vacuo
  4. customColumn purified by silica gel chromatography

Sources & evidence

ORD record
ord-86f069df3fce4cbc82d27a98ebbc3da4
Source dataset
uspto-grants-2016_07
Patent number
US09394308B2

Reaction notes

Loading…