Dichloromethane → HCID 66854295, compound

HRID 252117Notes

Reaction equation

HRID 252117 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[C:9]([O:13][C:14](=[O:21])[NH:15][C@H:16]1[CH2:20][CH2:19][NH:18][CH2:17]1)([CH3:12])([CH3:11])[CH3:10].C(N(C(C)C)C(C)C)C.ClCCl>C(#N)C>[C:9]([O:13][C:14](=[O:21])[NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([C:5]2[N:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH2:17]1)([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine

Product 1

HCID 66854295HCID 66854295, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Stir a solution of 5-bromo-2-chloropyrimidine (3.67 g, 19 mmol), (S)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (3.54 g, 19 mmol), and ethyldiisopropylamine (6.6 mL, 38 mmol) in acetonitrile (50 mL) at room temperature for 4 h. Pour into dichloromethane (200 mL) and wash with water (3×). Dry (sodium sulfate) and concentrate to give (S)-[1-(5-bromopyrimidin-2-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester as a tan solid (3.66 g, 71%).

Workup

  1. washwash with water (3×)
  2. dry with materialDry (sodium sulfate)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-89ef4a97f13c42ebbe5680729531a181
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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