Trifluoroacetic acid → 5-(3-(4-Fluorophenyl)oxetan-3-yl)-2-(piperazin-1-yl)pyrimidine

HRID 1498870Notes

Reaction equation

HRID 1498870 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[CH:13]=[N:14][C:15]([N:18]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]4)=[N:16][CH:17]=3)[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[CH:13]=[N:14][C:15]([N:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)=[N:16][CH:17]=3)[CH2:9][O:10][CH2:11]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118023292Tert-butyl 4-(5-(3-(4-fluorophenyl)oxetan-3-yl)pyrimidin-2-yl)piperazine-1-carboxylate

Product 1

HCID 1180227655-(3-(4-Fluorophenyl)oxetan-3-yl)-2-(piperazin-1-yl)pyrimidineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(5-(3-(4-fluorophenyl)oxetan-3-yl)pyrimidin-2-yl)piperazine-1-carboxylate (22 mg, 0.05 mmol) in DCM (1 mL) was treated with TFA (0.5 mL) at 60° C. for 3 h and then concentrated under reduced pressure. The residue (30 mg, crude, yellow solid, 100% yield) was directly used into the next step without further purification. MS (ES+) C17H19FN4O requires: 314. found 315 [M+H]+; purity: 87% (UV254).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue (30 mg, crude, yellow solid, 100% yield) was directly used into the next step without further purification

Sources & evidence

ORD record
ord-7d752818382943139112ebcb33bf0373
Source dataset
uspto-grants-2015_12
Patent number
US09200002B2

Reaction notes

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