Trifluoroacetic acid → Trifluoroacetic acid

HRID 1723803Notes

Reaction equation

HRID 1723803 reaction equation
C([O:8][C:9]1[CH:10]=[N:11][C:12]([N:15]2[CH2:20][CH2:19][N:18]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:17][CH2:16]2)=[N:13][CH:14]=1)C1C=CC=CC=1.[C:25]([OH:31])([C:27]([F:30])([F:29])[F:28])=[O:26]>>[CH3:24][S:21]([N:18]1[CH2:19][CH2:20][N:15]([C:12]2[N:11]=[CH:10][C:9]([OH:8])=[CH:14][N:13]=2)[CH2:16][CH2:17]1)(=[O:23])=[O:22].[C:25]([OH:31])([C:27]([F:30])([F:29])[F:28])=[O:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 688494605-(Benzyloxy)-2-[4-(methanesulfonyl)piperazin-1-yl]pyrimidine

Product 2

HCID 6422Trifluoroacetic acidHCID 68845735HCID 68845735, compound

Procedure

5-(benzyloxy)-2-[4-(methylsulfonyl)piperazin-1-yl]pyrimidine (57.9 g, 0.17 mol) was dissolved in TFA (600 mL) and the reaction heated to reflux, with stirring, for 7 hours then cooled to room temperature. The TFA was then in vacuo and the residue azeotroped with toluene (2×300 mL). The resulting solid was triturated with DCM, filtered off, washed with ether and dried to give 2-[4-(methylsulfonyl)piperazin-1-yl]pyrimidin-5-ol as a pale yellow solid (54.4 g, 0.15 mol, 88%, TFA salt).

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux
  3. customin vacuo and the residue azeotroped with toluene (2×300 mL)
  4. customThe resulting solid was triturated with DCM
  5. filtrationfiltered off
  6. washwashed with ether
  7. customdried

Sources & evidence

ORD record
ord-f56515aec78e4922a6c181a1a1778abf
Source dataset
uspto-grants-2009_02
Patent number
US07485644B2

Reaction notes

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