5-Bromo-2-chloropyrimidine → (S)-1-(5-bromopyrimidin-2-yl)-pyrrolidine-3-amine

HRID 252126Notes

Reaction equation

HRID 252126 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[NH2:9][C@H:10]1[CH2:14][CH2:13][NH:12][CH2:11]1>C(O)(C)C>[Br:8][C:5]1[CH:4]=[N:3][C:2]([N:12]2[CH2:13][CH2:14][C@H:10]([NH2:9])[CH2:11]2)=[N:7][CH:6]=1

Participants

4

Reactant 2

HCID 6066655-Bromo-2-chloropyrimidineHCID 1519351(3S)-(-)-3-Aminopyrrolidine

Product 1

HCID 66854146(S)-1-(5-bromopyrimidin-2-yl)-pyrrolidine-3-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Combine 2-chloro-5-bromopyrimidine (20.0 g, 1.0 eq) and isopropanol (200 mL). Add (S)-3-aminopyrrolidine (8.91 g, 1.0 eq) dropwise over about 30 minutes. Add isopropanol (10 mL) and heat to 50° C.-60′. After 4 hours, cool to 20° C.-25° C. over about 1 hour, stir for about 1 hour, and then collect the solid by filtration. Rinse the solid with isopropanol (2×25 mL) and dry under vacuum at about 40° C. to give (S)-1-(5-bromopyrimidin-2-yl)-pyrrolidine-3-amine as its hydrochloride salt.

Workup

  1. temperaturecool to 20° C.-25° C. over about 1 hour
  2. customcollect the solid
  3. filtrationby filtration
  4. washRinse the solid with isopropanol (2×25 mL)
  5. customdry under vacuum at about 40° C.

Sources & evidence

ORD record
ord-53d5ff9799934fe4aff23992677928d0
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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