Trifluoroacetic acid → Pyrimidine, 5-bromo-2-(1-propyl-3-pyrrolidinyl)-

HRID 1260240Notes

Reaction equation

HRID 1260240 reaction equation
CO[CH2:3][N:4]([CH2:11][CH2:12][CH3:13])[CH2:5][CH2:6][Si](C)(C)C.[Br:14][C:15]1[CH:16]=[N:17][C:18]([CH:21]=C)=[N:19][CH:20]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:14][C:15]1[CH:16]=[N:17][C:18]([CH:21]2[CH2:6][CH2:5][N:4]([CH2:11][CH2:12][CH3:13])[CH2:3]2)=[N:19][CH:20]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 536286645-bromo-2-ethenylpyrimidineHCID 86761882HCID 86761882, compound

Product 1

HCID 57470082Pyrimidine, 5-bromo-2-(1-propyl-3-pyrrolidinyl)-Yield 35.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Methoxymethyl-propyl-trimethylsilanylethyl-amine (14.13 g, 74.61 mmol) in CH2Cl2 (4 ml) was added dropwise to a 0° C. cooled solution of 5-bromo-2-vinyl-pyrimidine (2 g, 10.80 mmol) and TFA (210 μl, 2.72 mmol) in CH2Cl2 (45 ml) over a period of 20 min. The reaction mixture was then stirred at room temperature for 2 h. The crude material was diluted with CH2Cl2, washed with saturated aqueous NaHCO3 and the organic layer was dried over Na2SO4 and evaporated. The residue was chromatographied on silica gel (CH2Cl2:methanol, 97:3) to afford the title compound (1.03 g, 34%) as a brown oil.

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialthe organic layer was dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-10acffa648de49b48cec2deafb6a4dcf
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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