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

HRID 2262625Notes

Reaction equation

HRID 2262625 reaction equation
CO[CH2:3][N:4]([CH2:10][CH2:11][CH3:12])[CH2:5][Si](C)(C)C.[Br:13][C:14]1[CH:15]=[N:16][C:17]([CH:20]=[CH2:21])=[N:18][CH:19]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:13][C:14]1[CH:15]=[N:16][C:17]([CH:20]2[CH2:21][CH2:5][N:4]([CH2:10][CH2:11][CH3:12])[CH2:3]2)=[N:18][CH:19]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 536286645-bromo-2-ethenylpyrimidineHCID 53628665HCID 53628665, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Methoxymethyl-propyl-trimethylsilanylmethyl-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-00977c6c1c154faaba33dbe3a937f9f8
Source dataset
uspto-grants-2010_12
Patent number
US07851463B2

Reaction notes

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