Hydrochloric Acid → 4-[3-(4-{3-Trifluoromethylphenyl}piperazinyl)propylthio]pyrimidine

HRID 1278559Notes

Reaction equation

HRID 1278559 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.Cl[CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[CH2:14][CH2:13]1.C(N(CC)CC)C.Cl>CN(C=O)C>[F:27][C:24]([F:25])([F:26])[C:20]1[CH:19]=[C:18]([N:15]2[CH2:14][CH2:13][N:12]([CH2:11][CH2:10][CH2:9][S:1][C:2]3[CH:7]=[CH:6][N:5]=[CH:4][N:3]=3)[CH2:17][CH2:16]2)[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 3060362Piperazine, 1-(3-chloropropyl)-4-(3-(trifluoromethyl)phenyl)-HCID 178527731HCID 178527731, compound

Product 1

HCID 158170584-[3-(4-{3-Trifluoromethylphenyl}piperazinyl)propylthio]pyrimidineYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 g (13.4 mmol) of 4-mercaptopyrimidine, 4.3 g (14 mmol) of 1-(3-chloropropyl)-4-(3-trifluoromethylphenyl)piperazine and 1.5 g (15 mmol) of triethylamine in 5 ml of DMF were stirred at 100° C. for 1 hour. The mixture was then poured into 5% strength hydrochloric acid and extracted with MTB ether. The aqueous phase was made alkaline with sodium hydroxide solution and then extracted with ethyl acetate, and the organic phase was dried over MgSO4 and concentrated. The residue was purified by chromatography (mobile phase: CH2Cl2/CH3OH=98/2). 3.0 g of product were obtained as a yellowish oil (=59% yield).

Workup

  1. extractionextracted with MTB ether
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (mobile phase: CH2Cl2/CH3OH=98/2)

Sources & evidence

ORD record
ord-dcf0e05e74a84555a2f58dbd17d8d5f0
Source dataset
uspto-grants-2002_09
Patent number
US06444674B1

Reaction notes

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